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

HRID 1284108Notes

Reaction equation

HRID 1284108 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-d40baaa696ea488ab9f340c411b67d3d
Source dataset
uspto-grants-1976_08
Patent number
US03978064

Reaction notes

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