16357-59-8

Basic information

• Product Name: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline
• Synonyms: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline≥ 99% (HPLC);Ethyl 2-ethoxy-1,2-dihydro-1-quinolinecarboxylate for synthesis;EEDQ~N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline;ethyl N-(2-ethoxy-1,2-dihydroquinoline)carboxylate;EEDQ (1-ETHOXY-CARBONYL-2-ETHOXY-1,2;EEDQ, 99+%, (2-ETHOXY-1-ETHOXYCARBONYL-1 ,2-DIHYDROQUINOLINE);N-ETHOXYCARBONYL-2-ETHOXY-1,2-DIHYDROQUINOLINE 99% ( EEDQ);Eedq(2-Ethoxy-1-Ethoxycarbonyl-1,2-Dihydroquinoline)
• CAS NO: 16357-59-8
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.29
• EINECS: 240-418-2
• Product Categories: Acids and Derivatives;Heterocycles;Coupling Reagent;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry
• Mol File: 16357-59-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 62-67 °C(lit.)
• Boiling Point: 125-128 °C (0.1 mmHg)
• Flash Point: 125-128°C/0.1mm
• Appearance: White to beige/Crystalline Powder
• Density: 1.1173 (rough estimate)
• Vapor Pressure: 3.04E-05mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chlorofrom (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: -1.27±0.40(Predicted)
• Water Solubility: insoluble
• Sensitive: Moisture Sensitive
• Merck: 14,3518
• BRN: 533048
• CAS DataBase Reference: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(16357-59-8)
• EPA Substance Registry System: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(16357-59-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 38-36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26-36
• WGK Germany: 3
• RTECS: VB2010000
• F: 9-21
• TSCA: Yes
• Hazardous Substances Data: 16357-59-8(Hazardous Substances Data)

Usage

Chemical Properties

White to pale yellow solid

Uses

Different sources of media describe the Uses of 16357-59-8 differently. You can refer to the following data:
1. Peptide condensing agent with little or no racemization. Amidation coupling reagent.
2. In the synthesis of peptides.
3. 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline is an irreversible membrane-bound receptor antagonist. It is used in synthetic chemistry, discovery, process R&D. It also acts as coupling reagents.

Purification Methods

Dissolve EEDQ ~180g in CHCl3, evaporate to dryness in a vacuum. Add dry Et2O (20mL) and a white solid separates on standing. Set aside for a few hours, collect the solid, wash it thoroughly with cold Et2O and dry it in a vacuum (~140g, m 63.5-65o). A further crop of solid (~25g) is obtained from the filtrate on standing overnight. [Fieser & Fieser Reagents for Organic Synthesis 2 191 1969, Belleau et al. J Am Chem Soc 90 823 1968 and 90 1651 1968, Beilstein 21/3 V 28.]

InChI:InChI=1/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3/t13-/m1/s1

Synthetic route

quinoline (91-22-5) + ethanol (64-17-5) + chloroformic acid ethyl ester (541-41-3) → N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 0℃; for 1.33333h;	69%

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + acetone (67-64-1) → ethyl 4-(2-hydroxypropan-2-yl)quinoline-1(4H)-carboxylate

Conditions	Yield
With diethylzinc; palladium diacetate; triphenylphosphine In toluene at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; regioselective reaction;	100%

propylamine (107-10-8) + indole-3-glycolic acid (3050-37-1) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester (1H-indol-3-yl)-propylcarbamoyl-methyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

indole-3-glycolic acid (3050-37-1) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + aniline (62-53-3) → carbonic acid ethyl ester (1H-indol-3-yl)-phenylcarbamoyl-methyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

indole-3-glycolic acid (3050-37-1) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → ethoxycarbonyloxy-(1H-indol-3-yl)-acetic acid

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

propylamine (107-10-8) + 2-hydroxy-octanoic acid (617-73-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester 1-propylcarbamoyl-heptyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

propylamine (107-10-8) + phenyllactic acid (828-01-3) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester 2-phenyl-1-propylcarbamoyl-ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

phenyllactic acid (828-01-3) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → 2-ethoxycarbonyloxy-3-phenyl-propionic acid

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

phenyllactic acid (828-01-3) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + benzylamine (100-46-9) → carbonic acid 1-benzylcarbamoyl-2-phenyl-ethyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	99%

methyl 2-(bromomethyl)propenoate (4224-69-5) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → 2-(2-methoxycarbonyl-allyl)-2H-quinoline-1-carboxylic acid ethyl ester

Conditions	Yield
With indium; acetic acid In tetrahydrofuran for 0.5h;	99%

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + 3-methylthiophenylboronic acid (128312-11-8) → C19H19NO2S (1497411-35-4)

Conditions	Yield
With methallylnickel chloride dimer; sodium phenoxide; (1R,7R)-9,9-dimethyl-2,2,6,6-tetra(napht-2-yl)-4-phenyl-3,5,8,10-tetraoxa-4-phosphabicyclo<5.3.0>decane In 1,4-dioxane; tert-Amyl alcohol at 20℃; for 25h; Suzuki Coupling; Inert atmosphere; enantioselective reaction;	99%

indole-3-glycolic acid (3050-37-1) + di-n-propylamine (142-84-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid dipropylcarbamoyl-(1H-indol-3-yl)-methyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	98%

indole-3-glycolic acid (3050-37-1) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + benzylamine (100-46-9) → carbonic acid benzylcarbamoyl-(1H-indol-3-yl)-methyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	98%

MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + benzylamine (100-46-9) → ethoxycarbonyloxy-phenyl-acetic acid benzylamide (101730-29-4)

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	98%

2-hydroxy-octanoic acid (617-73-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + aniline (62-53-3) → carbonic acid ethyl ester 1-phenylcarbamoyl-heptyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	98%

di-n-propylamine (142-84-7) + MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid dipropylcarbamoyl-phenyl-methyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	97%

propylamine (107-10-8) + LACTIC ACID (849585-22-4) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester 1-propylcarbamoyl-ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	97%

phenyllactic acid (828-01-3) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + aniline (62-53-3) → carbonic acid ethyl ester 2-phenyl-1-phenylcarbamoyl-ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	97%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + bis[2-(diphenylphosphino)phenyl] ether (166330-10-5) → C50H43NNiO4P2

Conditions	Yield
Stage #1: bis(1,5-cyclooctadiene)nickel (0); bis[2-(diphenylphosphino)phenyl] ether In toluene at 23℃; for 0.333333h; Inert atmosphere; Stage #2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In toluene for 1h; Inert atmosphere;	97%

fur-2-ylboronic acid (13331-23-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → 2-furan-2-yl-2H-quinoline-1-carboxylic acid ethyl ester

Conditions	Yield
In dichloromethane at 20℃; for 1h;	96.4%

phenyllactic acid (828-01-3) + di-n-propylamine (142-84-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid 1-dipropylcarbamoyl-2-phenyl-ethyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	96%

t-Boc-L-valine (13734-41-3) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → Boc-Val-O-COOEt (98807-40-0)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one In dichloromethane at 23℃; for 2h;	95%

2-hydroxy-4-methylpentanoic acid (10303-64-7) + di-n-propylamine (142-84-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid 1-dipropylcarbamoyl-3-methyl-butyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	95%

2-hydroxy-octanoic acid (617-73-2) + di-n-propylamine (142-84-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid 1-dipropylcarbamoyl-heptyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	95%

propylamine (107-10-8) + 2-hydroxy-4-methylpentanoic acid (10303-64-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester 3-methyl-1-propylcarbamoyl-butyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	95%

2-hydroxy-4-methylpentanoic acid (10303-64-7) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + benzylamine (100-46-9) → carbonic acid 1-benzylcarbamoyl-3-methyl-butyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	95%

2-hydroxy-octanoic acid (617-73-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + benzylamine (100-46-9) → carbonic acid 1-benzylcarbamoyl-heptyl ester ethyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	95%

N-tert.-butoxycarbonyl-(3-benzothienyl)glycine + p-nitrobenzyl 7-amino-3-methyl-3-cephem-4-carboxylate + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → p-nitrobenzyl D,L-7-[N-tert.-butoxycarbonyl-(3-benzothienyl)glycylamido]-3-methyl-3-cephem-4-carboxylate

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In tetrahydrofuran; water; ethyl acetate; acetonitrile	95%

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → ethyl-3-azido-4-chloro-2-ethoxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
With chlorine azide In water; toluene at 20℃; for 0.0188889h; Flow reactor;	95%

propylamine (107-10-8) + MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) → carbonic acid ethyl ester phenyl-propylcarbamoyl-methyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	94%

MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) + N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (16357-59-8) + aniline (62-53-3) → carbonic acid ethyl ester phenyl-phenylcarbamoyl-methyl ester

Conditions	Yield
In dichloromethane for 5h; Ambient temperature;	94%

Upstream product

• 91-22-5 quinoline 
• 64-17-5 ethanol 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 3783-38-8 methyl isonicotinate N-oxide 
• 350235-72-2 6-methoxy-1-phenyl-2-(4-pyridinyl)-1H-benzimidazole 
• 196696-26-1 tert-Butyl 7-{3-[5-Chloro-2-hydroxy-3-(2-hydroxybenzyl)benzyl]-2-hydroxybenzamido}cephalosporanate 
• 106624-70-8 methyl (2S)-2-[[2-(t-butoxycarbonylamino)acetyl]amino]-3-phenylpropanoate 
• 121415-68-7 N-(t-butyloxycarbonyl)-L-serine-2-(diphenylmethylene)hydrazide 

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