Diphenyl Ether → 6,7-Dimethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 868145Notes

Reaction equation

HRID 868145 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH:12]=[C:13]([C:19]([O:21]CC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[NH:11][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]2=[O:21]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 2267691Diethyl 2-[(3,4-dimethoxyanilino)methylidene]propanedioate

Product 1

HCID 100391496,7-Dimethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl esterYield 65.2%

Conditions

Temperature
50 °C

Procedure

[[(3,4-Dimethoxyphenyl)amino]methylene]malonic acid, diethyl ester (60 g, 188.5 mmol) was added to hot diphenylether (bath temperature 275° C.) under stirring. After stirring for 15 minutes, the mixture was allowed to cool to 50° C. The resulting crystals were collected by suction, washed thoroughly with ether and dried in vacuo to yield 34.1 g of the title compound having a melting point of 297° C.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customThe resulting crystals were collected by suction
  3. washwashed thoroughly with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-af4275a0fe4941e5ba6efbb32112c6d7
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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