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550-44-7

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550-44-7 Usage

Chemical Properties

White powder

Uses

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene h and the selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one have been studied.

General Description

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene has been studied. The selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one in ionic liquids and phenol as a proton donor under silent and ultrasonic conditions has been reported. Single electron transfer (SET)-induced photochemical reaction of NMP with silyl enol ether has been investigated. Nitration of NMP is reported to afford “exclusively” 3-nitro-derivative.

Purification Methods

Recrystallise the imide from absolute EtOH or AcOH (m 134o). The IR has max at 1780 and 1380cm -1. [Beilstein 21 H 461, 21 III/IV 5030.]

Check Digit Verification of cas no

The CAS Registry Mumber 550-44-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 550-44:
(5*5)+(4*5)+(3*0)+(2*4)+(1*4)=57
57 % 10 = 7
So 550-44-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H7NO2/c1-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3

550-44-7 Well-known Company Product Price

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  • Alfa Aesar

  • (L08991)  N-Methylphthalimide, 98%   

  • 550-44-7

  • 5g

  • 184.0CNY

  • Detail
  • Alfa Aesar

  • (L08991)  N-Methylphthalimide, 98%   

  • 550-44-7

  • 25g

  • 796.0CNY

  • Detail
  • Aldrich

  • (407992)  N-Methylphthalimide  98%

  • 550-44-7

  • 407992-5G

  • 341.64CNY

  • Detail

550-44-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methylphthalimide

1.2 Other means of identification

Product number -
Other names 1H-Isoindole-1,3(2H)-dione, 2-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:550-44-7 SDS

550-44-7Synthetic route

methanol
67-56-1

methanol

phthalimide
136918-14-4

phthalimide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine Mitsunobu reaction;100%
With bis(3-(perfluoro-t-butyloxy)propyl)diazodicarboxylate; bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; Inert atmosphere;95%
With PhP(C6H4-p-(CH2)2C6F13)2; diethylazodicarboxylate In tetrahydrofuran91%
N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With hydrogenchloride at 20℃; under 750.06 Torr; Cyclization; solid-gas reaction;100%
With water
at 190℃;
at 190℃;
phthalimide
136918-14-4

phthalimide

trifluoroacetic acid-methyl ester
431-47-0

trifluoroacetic acid-methyl ester

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With sodium methylate; sodium hydride In dimethyl sulfoxide at 20℃; for 10h;100%
phthalimide
136918-14-4

phthalimide

formaldehyd
50-00-0

formaldehyd

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In water at 75 - 80℃; pH=5.5; Temperature; Concentration; Autoclave; Inert atmosphere;99.33%
at 150 - 160℃;
phthalic anhydride
85-44-9

phthalic anhydride

methylamine
74-89-5

methylamine

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
In water at 120 - 180℃; for 0.333333h; Autoclave; Inert atmosphere;99%
In ethanol; toluene for 3h; Solvent; Reflux;95%
In water91%
N-phthaloylglycine
4702-13-0

N-phthaloylglycine

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With acrylonitrile; β‐cyclodextrin In acetonitrile UV-irradiation; Inert atmosphere;97%
With potassium carbonate In water; acetone at 15℃; Irradiation;95%
In acetonitrile for 1h; Kinetics; Mechanism; Irradiation; Variation of solvents, irradiation times and methods.;94%
phthalimide
136918-14-4

phthalimide

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 8h;95%
2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

carbon monoxide
201230-82-2

carbon monoxide

methylamine
74-89-5

methylamine

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With triethylamine In toluene at 100℃; under 760.051 Torr; for 4h; Autoclave;95%
formic acid
64-18-6

formic acid

2-iodo-N-methyl-benzamide
58084-22-3

2-iodo-N-methyl-benzamide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With iodine; palladium diacetate; triethylamine; triphenylphosphine In toluene at 80℃; for 2h;95%
N-methylbenzamide
88070-48-8

N-methylbenzamide

carbon monoxide
201230-82-2

carbon monoxide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With potassium dihydrogenphosphate; Cp*Rh(MeCN)3[ClO4]2; silver carbonate In tert-Amyl alcohol at 100℃; under 760.051 Torr; for 24h;94%
N-methyl-1,2,5,6-tetrahydrophthalimide
2021-21-8

N-methyl-1,2,5,6-tetrahydrophthalimide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With palladium (II) trifluoroacetate; sodium anthraquinone-2-sulfonate; oxygen; magnesium sulfate In chlorobenzene at 110℃; under 760.051 Torr; for 24h; Sealed tube;94%
methyl N-methyl-N-carbethoxyphthalamate
109124-50-7

methyl N-methyl-N-carbethoxyphthalamate

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With sodium In toluene for 2h; Heating;93%
2-(methylcarbamoyl)benzoic acid.
6843-36-3

2-(methylcarbamoyl)benzoic acid.

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
In water; toluene for 3h; Heating;93%
3-(p-tolylimino)-isoindolinone
135354-98-2

3-(p-tolylimino)-isoindolinone

methyl iodide
74-88-4

methyl iodide

A

N-methylphthalimide
550-44-7

N-methylphthalimide

B

(E)-2-methyl-3-(p-tolylimino)-isoindolinone
84628-32-0

(E)-2-methyl-3-(p-tolylimino)-isoindolinone

C

3-N-methyl-N(p-tolyl)amino-isoindoleninone
84628-34-2

3-N-methyl-N(p-tolyl)amino-isoindoleninone

Conditions
ConditionsYield
In toluene at 120℃; for 24h; in a pressure tubing;A 2%
B 6%
C 92%
phthalimide
136918-14-4

phthalimide

methyl iodide
74-88-4

methyl iodide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With potassium hydroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 5h;91%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;90%
With potassium fluoride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 25℃; for 5h;88%
phthalimide
136918-14-4

phthalimide

N,N'-dicyclohexyl-O-methyl isourea
6257-10-9

N,N'-dicyclohexyl-O-methyl isourea

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 2h;90%
N-methoxyphthalimide
1914-20-1

N-methoxyphthalimide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With triisopropyl phosphite; acetic acid at 100℃; for 15h;90%
methylamine
74-89-5

methylamine

dimethyl (1-chloro-1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate
17858-14-9

dimethyl (1-chloro-1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.166667h;89%
sodium phthalimide
33081-78-6

sodium phthalimide

[(E)-2-(4-chlorophenyl)ethenyl]dimethylsulfonium triflate

[(E)-2-(4-chlorophenyl)ethenyl]dimethylsulfonium triflate

A

N-methylphthalimide
550-44-7

N-methylphthalimide

B

(E)-4-chlorostyryl methyl sulfide
25650-51-5

(E)-4-chlorostyryl methyl sulfide

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 20℃;A 58%
B 88%
N-phthalimidyl-2-aminoacetaldehyde
2913-97-5

N-phthalimidyl-2-aminoacetaldehyde

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane In diethylene glycol dimethyl ether for 16h; Heating;87%
(E)-2-(4-(dimethylamino)-2-oxobut-3-enyl)isoindoline-1,3-dione
746677-26-9

(E)-2-(4-(dimethylamino)-2-oxobut-3-enyl)isoindoline-1,3-dione

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With zeolite at 160℃; for 0.5h; Microwave irradiation; Neat (no solvent);87%
2-iodo-N-methyl-benzamide
58084-22-3

2-iodo-N-methyl-benzamide

phenyl formate
1864-94-4

phenyl formate

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; N,N,N,N,-tetramethylethylenediamine; triethylamine at 80℃; for 18h; Inert atmosphere; Schlenk technique;87%
N-chlorophthalimide
3481-09-2

N-chlorophthalimide

methyl iodide
74-88-4

methyl iodide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.1h;87%
endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide
155793-97-8

endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide

A

N-methylphthalimide
550-44-7

N-methylphthalimide

B

N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide
99529-42-7

N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide

Conditions
ConditionsYield
With hydrogen; silver; zinc In tetrahydrofuran for 0.0833333h; Heating;A 15%
B 85%
N-(benzylthio)phthalimide
14204-26-3

N-(benzylthio)phthalimide

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

N-methylphthalimide
550-44-7

N-methylphthalimide

B

O,O-dimethyl S-(benzyl) phosphorothioate
7205-16-5

O,O-dimethyl S-(benzyl) phosphorothioate

Conditions
ConditionsYield
In toluene Ambient temperature;A n/a
B 85%
N-methyl-2-formylbenzamide
117194-00-0

N-methyl-2-formylbenzamide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
Stage #1: N-methyl-2-formylbenzamide With copper(I) bromide In tetrachloromethane; acetonitrile at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With N-Bromosuccinimide In tetrachloromethane; acetonitrile at 75℃; for 12h; Inert atmosphere;
85%
N-<(Trimethylsilyl)methyl>phthalimide
18042-62-1

N-<(Trimethylsilyl)methyl>phthalimide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
In acetonitrile Irradiation;83%
In acetonitrile for 24h; Irradiation;81%
N-Octadecylthiophthalimid
122504-70-5

N-Octadecylthiophthalimid

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

N-methylphthalimide
550-44-7

N-methylphthalimide

B

Thiophosphoric acid O,O'-dimethyl ester S-octadecyl ester
128371-61-9

Thiophosphoric acid O,O'-dimethyl ester S-octadecyl ester

Conditions
ConditionsYield
In toluene Ambient temperature;A n/a
B 83%
potassium phtalimide
1074-82-4

potassium phtalimide

methyl iodide
74-88-4

methyl iodide

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Ambient temperature;82%
In N,N-dimethyl-formamide for 1h; Reflux;80%
at 150℃;
In N,N-dimethyl-formamide for 3h; Ambient temperature;
In N,N-dimethyl-formamide for 1h; Reflux;
C28H18CuN4O4
16050-53-6

C28H18CuN4O4

N-methylphthalimide
550-44-7

N-methylphthalimide

Conditions
ConditionsYield
With di-tert-butyl peroxide; bis(1-methyl-1-phenylethyl)peroxide In acetonitrile at 100℃; for 18h; Inert atmosphere; Glovebox;81%
N-methylphthalimide
550-44-7

N-methylphthalimide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

3-hydroxy-2-methyl-3-phenyl-2,3-dihydro-isoindol-1-one
26597-63-7

3-hydroxy-2-methyl-3-phenyl-2,3-dihydro-isoindol-1-one

Conditions
ConditionsYield
Stage #1: N-methylphthalimide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 3h; Grignard reaction; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; diethyl ether Grignard reaction;
100%
N-methylphthalimide
550-44-7

N-methylphthalimide

2-(hydroxymethyl)-N-methylbenzamide
39976-03-9

2-(hydroxymethyl)-N-methylbenzamide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium tert-butylate; hydrogen In tetrahydrofuran; isopropyl alcohol at 40℃; under 30003 Torr; for 15h; Autoclave; Sealed tube;99%
With sodium tetrahydroborate In water; isopropyl alcohol; toluene at 0℃; for 4h; Yield given;
With sodium tetrahydroborate In water; isopropyl alcohol; toluene
N-methylphthalimide
550-44-7

N-methylphthalimide

5-bromo-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione
90224-73-0

5-bromo-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

Conditions
ConditionsYield
With sulfuric acid; 5,5-dibromohydantoin at 20℃; for 6h; Sealed tube;98.4%
N-methylphthalimide
550-44-7

N-methylphthalimide

3-hydroxy-2-methyl-isoindolin-1-one
29879-69-4

3-hydroxy-2-methyl-isoindolin-1-one

Conditions
ConditionsYield
With hydrogen; sodium hydroxide In toluene at 40℃; under 30003 Torr; for 24h;97%
With ethanol; tetrabutylammonium tetrafluoroborate; diisopropylamine at 20℃; for 2h; Electrochemical reaction; Schlenk technique; Green chemistry; chemoselective reaction;91%
With acetic acid; zinc at 60℃; for 0.166667h;75%
N-methylphthalimide
550-44-7

N-methylphthalimide

acrylonitrile
107-13-1

acrylonitrile

3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionitrile
1001428-10-9

3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionitrile

Conditions
ConditionsYield
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran at -30℃; for 1.5h;97%
With ammonia; water; zinc In dichloromethane at 20℃; under 760.051 Torr; for 4h; Cooling with ice;81%
N-methylphthalimide
550-44-7

N-methylphthalimide

2-methylisoindoline
3474-87-1

2-methylisoindoline

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;96%
With borane In tetrahydrofuran for 6h; Reflux;80%
With sulfuric acid at 85℃; Electrolysis.Verwendung einer amalgamierten Zink-Kathode;
N-methylphthalimide
550-44-7

N-methylphthalimide

4-nitro-N-methyl-phthalimide
41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 60℃; for 0.05h; Temperature;96%
With sulfuric acid; nitric acid at 30℃; for 3h; Temperature;94%
With sulfuric acid; potassium nitrate at -5 - 40℃; for 4h; Reagent/catalyst; Temperature;91%
N-methylphthalimide
550-44-7

N-methylphthalimide

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-hydroxy-1,2-dimethyl-2,3-dihydro-3-oxo-1H-isoindole
29879-71-8

1-hydroxy-1,2-dimethyl-2,3-dihydro-3-oxo-1H-isoindole

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -30 - -5℃; for 2h;96%
N-methylphthalimide
550-44-7

N-methylphthalimide

C10H10NO3(1-)*K(1+)
1238840-05-5

C10H10NO3(1-)*K(1+)

N-[(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)methyl]-N-phenylacetamide
1238840-23-7

N-[(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)methyl]-N-phenylacetamide

Conditions
ConditionsYield
In water; acetone at 15 - 20℃; for 1h; UV-irradiation; Inert atmosphere;95%
methanol
67-56-1

methanol

N-methylphthalimide
550-44-7

N-methylphthalimide

2,3-dihydro-3-methoxy-2-methyl-1H-isoindol-1-one

2,3-dihydro-3-methoxy-2-methyl-1H-isoindol-1-one

Conditions
ConditionsYield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 90℃; under 15001.5 Torr; for 18h; Kinetics; Catalytic behavior; Temperature; Pressure; Reagent/catalyst; Sealed tube; Autoclave; Green chemistry;95%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;
N-methylphthalimide
550-44-7

N-methylphthalimide

pentan-1-ol
71-41-0

pentan-1-ol

C14H19NO2

C14H19NO2

Conditions
ConditionsYield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;95%
N-methylphthalimide
550-44-7

N-methylphthalimide

bromopentene
1119-51-3

bromopentene

C14H17NO

C14H17NO

Conditions
ConditionsYield
Stage #1: bromopentene With magnesium In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: N-methylphthalimide In tetrahydrofuran at -20℃; for 1h; Inert atmosphere;
Stage #3: With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -20 - 0℃; for 0.5h; Inert atmosphere;
95%
N-methylphthalimide
550-44-7

N-methylphthalimide

isopropyl alcohol
67-63-0

isopropyl alcohol

C12H15NO2

C12H15NO2

Conditions
ConditionsYield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;94%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Autoclave;87%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

N-methylphthalimide
550-44-7

N-methylphthalimide

A

1,1,4-triphenyl-1,2,3,4-tetrahydronaphthalene
41977-31-5

1,1,4-triphenyl-1,2,3,4-tetrahydronaphthalene

B

3-(diphenylmethylene)-2-methyl-2,3-dihydro-1H-isoindole-1-one
92172-54-8

3-(diphenylmethylene)-2-methyl-2,3-dihydro-1H-isoindole-1-one

C

6,7-dihydro-6,6-diphenyl-1-methyl-3,4-benzazepine-2,5-dione
95363-11-4

6,7-dihydro-6,6-diphenyl-1-methyl-3,4-benzazepine-2,5-dione

Conditions
ConditionsYield
In acetonitrile for 3h; Mechanism; also in the presence of phenanthrene;A 93%
B 10%
C 11%
In acetonitrile for 3h; Irradiation;A 93%
B 10%
C 11%
N-methylphthalimide
550-44-7

N-methylphthalimide

ethyl cinnamate
4192-77-2

ethyl cinnamate

3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)3-phenylpropionic acid ethyl ester

3-(1-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)3-phenylpropionic acid ethyl ester

Conditions
ConditionsYield
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran at 0℃; for 3h;93%
N-methylphthalimide
550-44-7

N-methylphthalimide

potassium (2-methylphenoxy)acetate
67433-97-0

potassium (2-methylphenoxy)acetate

C17H17NO3
1197155-41-1

C17H17NO3

Conditions
ConditionsYield
In water; acetone at 15 - 20℃; for 1h; Irradiation; Inert atmosphere;93%
N-methylphthalimide
550-44-7

N-methylphthalimide

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

3-(2-methoxyethoxy)-2-methylisoindolin-1-one

3-(2-methoxyethoxy)-2-methylisoindolin-1-one

Conditions
ConditionsYield
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In neat (no solvent) at 90℃; under 15001.5 Torr; for 18h; Sealed tube; Autoclave; Green chemistry;93%
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Autoclave;90%

550-44-7Relevant articles and documents

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Sato,Y. et al.

, p. 4565 - 4568 (1973)

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A convenient method of N-methylphthalimide synthesis

Vasilevskaya,Yakovleva,Kobrin

, p. 2463 - 2465 (1995)

We suggest a convenient method to obtain N-methylphthalimide with a high yield in the reaction of phthalic anhydride with aqueous methylamine.

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Mazzocchi,P.H. et al.

, p. 3079 - 3080 (1978)

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Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams

Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao

supporting information, p. 2298 - 2302 (2021/04/05)

An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.

Preparation of alkylated compounds using the trialkylphosphate

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Paragraph 0184-0185; 0208, (2021/11/02)

[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate

Lai, Huifang,Lin, Jin,Xu, Jiexin,Zha, Daijun

supporting information, p. 7621 - 7626 (2021/09/22)

Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, we describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Additionally, the reaction mechanism appears to involve a radical and a carbocationic pathway.

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