Isopropylamine → 3-Isopropylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

HRID 328806Notes

Reaction equation

HRID 328806 reaction equation
O[CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23].[CH:24]([NH2:27])([CH3:26])[CH3:25]>C1C=CC=CC=1>[CH:24]([NH:27][CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 70638946Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 867338853-Isopropylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3.2 g. of 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester in 30 ml. of benzene containing 650 mg. of isopropylamine is allowed to stir at room temperature for 48 hrs. The reaction solution is concentrated to give 4 g. of a yellow foam which could not be induced to crystallize.

Workup

  1. concentrationThe reaction solution is concentrated
  2. customto give 4 g
  3. customto crystallize

Sources & evidence

ORD record
ord-ce3cb90e9ecd4317b781180862a6e00c
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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