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173140-90-4

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173140-90-4 Usage

Uses

5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

A 5 liter flask equipped with a mechanical stirrer, thermometer, and refluxing condenser was charged with 8-benzyloxy-5-[(R)-(2-bromo-1-hydroxyethyl)]-carbostyriI (70gms/0.187 moles), potassium carbonate (74 gmsl 0.536 moles), acetone (3.5 liters) and water (35 ml). The resulting slurry 'was heated to reflux and maintained for 2% hours. After completion of reaction, the hot mass was filtered on hylo bed to remove inorganics. The residue was slurried in dichloromethane (200 ml) and filtered on hyflo bed. The filtrates were combined together and concentrated under vacuum completely. The residue was dissolved. in dichloromethane (500ml) and filtered on hyflo bed to remove traces of insolubles and washed with dichloromethane(100 ml). The clear filtrate was distilled completely to obtain residue. The residue was charged with methanol (70 ml), stirred and heated to 50°C for 30 minutes. The slurry obtained was cooled to 25-30°C,chilled to 0- 5°C, stirred for 1 hour. The resulting solid was isolated by filtration, washed with methanol (30ml), followed by diisopropylether (100ml) and dried under vacuum at 60-65 °C for 10-12 hours to yield 40-41 gms of 8-benzyloxy- 5-(R)-oxiranylcarbostyril.

Check Digit Verification of cas no

The CAS Registry Mumber 173140-90-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,3,1,4 and 0 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 173140-90:
(8*1)+(7*7)+(6*3)+(5*1)+(4*4)+(3*0)+(2*9)+(1*0)=114
114 % 10 = 4
So 173140-90-4 is a valid CAS Registry Number.

173140-90-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one

1.2 Other means of identification

Product number -
Other names 2(1H)-Quinolinone,5-(2R)-oxiranyl-8-(phenylmethoxy)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:173140-90-4 SDS

173140-90-4Synthetic route

8-(phenylmethoxy)-5-((R)-2-chloro-1-hydroxy-ethyl)-(1H)-quinolin-2-one

8-(phenylmethoxy)-5-((R)-2-chloro-1-hydroxy-ethyl)-(1H)-quinolin-2-one

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
With potassium carbonate In water; acetone for 5 - 10h; Heating / reflux;
With potassium carbonate In water; acetone for 5 - 10h; Heating / reflux;
With potassium carbonate In water; butanone Product distribution / selectivity; Heating / reflux;
With potassium carbonate In water; acetone Product distribution / selectivity; Heating / reflux;
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
With potassium carbonate In water; acetone for 2.5h; Product distribution / selectivity; Heating / reflux;
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one
100331-89-3

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 0 - 2℃; for 1.75h;
Stage #2: With piperidine; water In tetrahydrofuran; toluene at 0 - 2℃; for 1h; Product distribution / selectivity;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
1.2: 0.25 - 0.33 h
2.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
8-quinolinol
148-24-3

8-quinolinol

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C
1.2: 15.25 - 16.33 h / 25 - 70 °C
1.3: 0.25 - 0.33 h / 0 - 30 °C
2.1: hydrogenchloride; water / 0.25 - 0.33 h
3.1: potassium carbonate / acetone / 14 h / Heating / reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
5.1: acetic anhydride / 2 h / 25 - 40 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
6.2: 4.5 h / Heating / reflux
6.3: 30 °C / pH 8 - 9
7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
7.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C
1.2: 15.25 - 16.33 h / 25 - 70 °C
1.3: 0.25 - 0.33 h / 0 - 30 °C
2.1: hydrogenchloride; water / 0.25 - 0.33 h
3.1: potassium carbonate / acetone / 14 h / Heating / reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
5.1: acetic anhydride / 2 h / 25 - 40 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
6.2: 4.5 h / Heating / reflux
6.3: 30 °C / pH 8 - 9
7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
7.2: 0.25 - 0.33 h
8.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
5-acetyl-8-hydroxyquinoline
2598-31-4

5-acetyl-8-hydroxyquinoline

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
5.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
5.2: 0.25 - 0.33 h
6.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
1-(8-benzyloxyquinolin-5-yl)ethanone
26872-48-0

1-(8-benzyloxyquinolin-5-yl)ethanone

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
2.1: acetic anhydride / 2 h / 25 - 40 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
3.2: 4.5 h / Heating / reflux
3.3: 30 °C / pH 8 - 9
4.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
4.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
2.1: acetic anhydride / 2 h / 25 - 40 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
3.2: 4.5 h / Heating / reflux
3.3: 30 °C / pH 8 - 9
4.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
4.2: 0.25 - 0.33 h
5.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
5-Acetyl-8-benzyloxyquinoline-N-oxide
100331-93-9

5-Acetyl-8-benzyloxyquinoline-N-oxide

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic anhydride / 2 h / 25 - 40 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
2.2: 4.5 h / Heating / reflux
2.3: 30 °C / pH 8 - 9
3.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
3.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 4 steps
1.1: acetic anhydride / 2 h / 25 - 40 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
2.2: 4.5 h / Heating / reflux
2.3: 30 °C / pH 8 - 9
3.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
3.2: 0.25 - 0.33 h
4.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
5-acetyl-8-hydroxyquinoline hydrochloride
57434-96-5

5-acetyl-8-hydroxyquinoline hydrochloride

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride; water / 0.25 - 0.33 h
2.1: potassium carbonate / acetone / 14 h / Heating / reflux
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
4.1: acetic anhydride / 2 h / 25 - 40 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
5.2: 4.5 h / Heating / reflux
5.3: 30 °C / pH 8 - 9
6.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
6.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 7 steps
1.1: hydrogenchloride; water / 0.25 - 0.33 h
2.1: potassium carbonate / acetone / 14 h / Heating / reflux
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
4.1: acetic anhydride / 2 h / 25 - 40 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
5.2: 4.5 h / Heating / reflux
5.3: 30 °C / pH 8 - 9
6.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
6.2: 0.25 - 0.33 h
7.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
benzyl bromide
100-39-0

benzyl bromide

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
5.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
5.2: 0.25 - 0.33 h
6.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
5-acetyl-8-benzyloxy-1H-quinolin-2-one
93609-84-8

5-acetyl-8-benzyloxy-1H-quinolin-2-one

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
1.2: 4.5 h / Heating / reflux
1.3: 30 °C / pH 8 - 9
2.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
2.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 3 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
1.2: 4.5 h / Heating / reflux
1.3: 30 °C / pH 8 - 9
2.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
2.2: 0.25 - 0.33 h
3.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

N-benzyltyramine
52447-50-4

N-benzyltyramine

C33H32N2O4
630127-17-2

C33H32N2O4

Conditions
ConditionsYield
In toluene at 100℃; for 12h;88%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

D-glucoheptonic acid
87-74-1

D-glucoheptonic acid

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one glucoheptonic acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one glucoheptonic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine at 90℃; for 5h;
Stage #2: D-glucoheptonic acid In ethanol at 60℃; for 0.0833333h;
81.2%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one 4-acetamidobenzoic acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one 4-acetamidobenzoic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine at 100℃; for 5h;
Stage #2: p-(acetylamino)benzoic acid In ethanol at 60℃; for 0.0833333h;
80.4%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

D-galacturonic acid
685-73-4

D-galacturonic acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one galacturonic acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one galacturonic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In butanone at 70℃; for 6h;
Stage #2: D-galacturonic acid In ethanol; butanone at 60℃; for 0.0833333h;
79.8%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

meso-tartaric acid
147-73-9

meso-tartaric acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one tartaric acid

5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one tartaric acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In cyclohexanone at 80℃; for 6h;
Stage #2: meso-tartaric acid In ethanol; cyclohexanone at 60℃; for 0.0833333h;
78.3%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-methoxybenzoic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-methoxybenzoic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In dimethyl sulfoxide at 110℃; for 7h;
Stage #2: 4-methoxybenzoic acid In ethanol; dimethyl sulfoxide at 60℃;
70.1%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

A

8-(benzyloxy)-5-(1-(5,6-diethyl-2,3-dihydro-1H-inden-2-ylamino)-2-hydroxyethyl)quinolin-2(1H)-one

8-(benzyloxy)-5-(1-(5,6-diethyl-2,3-dihydro-1H-inden-2-ylamino)-2-hydroxyethyl)quinolin-2(1H)-one

B

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one hydrochloride

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one hydrochloride

C

C49H49N3O6

C49H49N3O6

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 110℃; for 15h; Heating / reflux;A 7.8%
B 68.7%
C 12.4%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

A

Indacaterol hydrochloride

Indacaterol hydrochloride

B

C31H34N2O3*ClH

C31H34N2O3*ClH

C

C49H49N3O6*ClH

C49H49N3O6*ClH

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In diethylene glycol dimethyl ether at 110℃; for 15h;
Stage #2: With hydrogenchloride Product distribution / selectivity;
A 68.7%
B 7.8%
C 12.4%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

benzyl-(4,5,6,7-tetramethyl-indan-2yl)-1-amine
312753-89-2

benzyl-(4,5,6,7-tetramethyl-indan-2yl)-1-amine

C38H40N2O3
312754-35-1

C38H40N2O3

Conditions
ConditionsYield
In butan-1-ol at 110℃; for 22h;67%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

p-Toluic acid
99-94-5

p-Toluic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-toluic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-toluic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In dimethyl sulfoxide at 110℃; for 7h;
Stage #2: p-Toluic acid In ethanol; dimethyl sulfoxide at 60℃;
63.5%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-nitrobenzoic acid

5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-phenylmethoxy-(1H)-quinolin-2-one p-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In dimethyl sulfoxide at 110℃; for 7h;
Stage #2: 4-nitro-benzoic acid In ethanol; dimethyl sulfoxide at 60℃;
63%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-Dimethoxy-2-indanylamine
83598-55-4

5,6-Dimethoxy-2-indanylamine

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-dimethoxyindan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-25-5

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-dimethoxyindan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;36%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

2-amino-5,6-di-n-butylindan
312753-59-6

2-amino-5,6-di-n-butylindan

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-di-n-butylindan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-24-4

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-di-n-butylindan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;34%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C13H19N
789489-14-1

C13H19N

C31H34N2O3

C31H34N2O3

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 180℃; for 0.133333h; Microwave irradiation;31%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

2,3-dihydro-1H-inden-2-amine
2975-41-9

2,3-dihydro-1H-inden-2-amine

8-benzyloxy-5-[(R)-1-hydroxy-2-(indan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-21-1

8-benzyloxy-5-[(R)-1-hydroxy-2-(indan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;30%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2-methyl-indan-2-ylamine
312754-11-3

5,6-diethyl-2-methyl-indan-2-ylamine

C32H36N2O3
312754-19-1

C32H36N2O3

Conditions
ConditionsYield
In butan-1-ol at 100℃; for 1.25h; Microwave irradiation;30%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

benzyl bromide
100-39-0

benzyl bromide

C25H21NO3

C25H21NO3

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In toluene at 50℃; for 6h;30%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one
435273-75-9

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;28%
In diethylene glycol dimethyl ether at 108 - 114℃; Inert atmosphere;
In dimethyl sulfoxide for 18h; Reflux; Large scale;
In butan-1-ol at 120℃; for 6h; Temperature;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

2-amino-5,6-dimethylindan
162752-07-0

2-amino-5,6-dimethylindan

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-dimethylindan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-22-2

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-dimethylindan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;27%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

2-amino-4,7-diethylindan
312753-56-3

2-amino-4,7-diethylindan

8-hydroxy-5-[(R)-1-hydroxy-2-(4,7-diethylindan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-26-6

8-hydroxy-5-[(R)-1-hydroxy-2-(4,7-diethylindan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;22%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

2-amino-5,6-di-n-propylindan
312753-60-9

2-amino-5,6-di-n-propylindan

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-di-n-propylindan-2-ylamino)-ethyl]-1H-quinolin-2-one
1225285-23-3

8-benzyloxy-5-[(R)-1-hydroxy-2-(5,6-di-n-propylindan-2-ylamino)-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In butan-1-ol at 110℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation; regioselective reaction;21%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C16H29NSi

C16H29NSi

8-benzyloxy-5-[R-2-(5,6-diethyl-2,3,4,7-tetrahydro-1H-inden-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one
774222-38-7

8-benzyloxy-5-[R-2-(5,6-diethyl-2,3,4,7-tetrahydro-1H-inden-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 36h;21%
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

benzylamine
100-46-9

benzylamine

8-benzyloxy-5-[(R)-2-benzylamino-1-hydroxyethyl]-(1H)-quinolin-2-one
662111-65-1

8-benzyloxy-5-[(R)-2-benzylamino-1-hydroxyethyl]-(1H)-quinolin-2-one

Conditions
ConditionsYield
at 150℃; for 0.25h; Microwave rewactor;
at 150℃; for 0.25h; Microwave oven;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C26H26N4O2S

C26H26N4O2S

C44H41N5O5S
1064594-84-8

C44H41N5O5S

Conditions
ConditionsYield
In dichloromethane; isopropyl alcohol at 70℃; for 40h; Heating / reflux;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C25H29N3O3S

C25H29N3O3S

C43H44N4O6S
1064594-80-4

C43H44N4O6S

Conditions
ConditionsYield
In isopropyl alcohol at 70℃; for 24h; Heating / reflux;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C16H20N2O

C16H20N2O

C34H35N3O4
1055276-56-6

C34H35N3O4

Conditions
ConditionsYield
In isopropyl alcohol at 70℃; for 36h; Heating / reflux;
In isopropyl alcohol
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

C28H28N2O

C28H28N2O

C46H43N3O4
1055276-52-2

C46H43N3O4

Conditions
ConditionsYield
In isopropyl alcohol at 70℃; for 34h; Heating / reflux;
In isopropyl alcohol at 78℃; for 16h;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

8-benzyloxy-5-[R-1-hydroxy-2-(2,3,4,7-tetrahydro-1H-inden-2-ylamino)ethyl]-1H-quinolin-2-one
774222-36-5

8-benzyloxy-5-[R-1-hydroxy-2-(2,3,4,7-tetrahydro-1H-inden-2-ylamino)ethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
Stage #1: 2,3,4,7-tetrahydro-1H-inden-2-ylamine With N,O-bis-(trimethylsilyl)-acetamide In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;
Stage #2: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone In DMF (N,N-dimethyl-formamide) at 80℃; for 96h; Heating / reflux;
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

8-benzyloxy-5-[R-2-(S-5-(furan-2-yl)-indan-2-ylamino)-1-hydroxyethyl]-1H-quinolin-2-one
774222-67-2

8-benzyloxy-5-[R-2-(S-5-(furan-2-yl)-indan-2-ylamino)-1-hydroxyethyl]-1H-quinolin-2-one

Conditions
ConditionsYield
Stage #1: S-5-(furan-2-yl)indan-2-ylamine With N,O-bis-(trimethylsilyl)-acetamide In DMF (N,N-dimethyl-formamide) for 0.5h;
Stage #2: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone In DMF (N,N-dimethyl-formamide) at 85℃; for 48h; Heating / reflux;

173140-90-4Relevant articles and documents

PROCESS FOR PREPARING ISOMERS OF CARMOTEROL

-

, (2008/12/07)

A process for preparing a compound of formula (III) comprising condensing an oxiranyl compound of formula (I) with an amine of formula (II) or a salt thereof wherein: R1 is a group selected from alkyl, aryl, allyl, alkoxy, cycloalkyl, heterocyclic, alkenyl, benzocycloalkyl, aralkyl, haloarylalkyl, heteroaralkyl, haloalkyl, alkoxyaralkyl, substituted silyl and benzyl; and R2 is hydrogen, optionally substituted silyl or optionally substituted benzyl. Formula (I), (II) and (III): There is also described a process for preparing (R,R)-carmoterol from compound (III).

A PROCESS FOR THE PREPARATION OF 5-(HALOACETYL)-8-(SUBSTITUTED OXY)-(1H)-QUINOLIN-2-ONES

-

Page 30-31, (2008/06/13)

The invention relates to a process for preparing 5-(α-haloacetyl)-8-substituted oxy-(1H)-quinolin-2-ones. The process involves (i) reacting (a) 8-hydroxy-(1H)-quinolin-2-one with an acylating agent and a Lewis acid to form 5-acetyl-8-hydroxy-(1H)-quinolin-2-one; or (b) 8-hydroxy-(lH)-quinolin-2-one with an acylating agent to form 8-acetoxy-(lH)-quinolin-2-one, and treating, in-situ, the 8-acetoxy-(1H)-quinolin-2-one with a Lewis acid to form 5-acetyl-8-hydroxy-(1H)-quinolin-2-one; or (c) 8-acetoxy-(1H)-quinolin-2-one with a Lewis acid to form 5-acetyl-8-hydroxy-(lH)-quinolin-2-one; (ii) reacting the 5-acetyl-8-hydroxy-(1H)-quinolin-2-one prepared in Step (i) with a compound having the Formula RL in the presence of a base and a solvent to form 5-acetyl-8-substituted oxy-(1H)-quinolin-2-one, wherein R is a protecting group and L is a leaving group; and (iii) reacting the 5-acetyl-8-substituted oxy-(1H)-quinolin-2-one with a halogenating agent in the presence of a solvent to form a 5-(α-haloacetyl)-8-substituted oxy-(1H)-quinolin-2-one.

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