Ethyl formate → 6-Chloro-3-hydroxymethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653129Notes

Reaction equation

HRID 653129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][CH2:6][C:5]2=[O:16].[CH:17](OCC)=[O:18]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][C:6](=[CH:17][OH:18])[C:5]2=[O:16]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 145014226-Chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 678721806-Chloro-3-hydroxymethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (200.5 g) and 1,5-diazabicyclo[5,4,0 ]undecene-5 (384.9 g) in ethyl formate (400.9 g) was heated at 55° C. with stirring for 7 hours and then diluted with cold water (450 ml). The mixture was washed successively with diisopropyl ether and ethyl acetate and then the aqueous layer was acidified with hydrochloric acid under ice cooling. The resultant precipitate was collected by filtration and dried to give 6-chloro-3-hydroxymethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (168.29 g).

Workup

  1. washThe mixture was washed successively with diisopropyl ether and ethyl acetate
  2. filtrationThe resultant precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-ea6acacad165474ab0219d6f244cd3d5
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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