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

HRID 35679
Notes
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Reaction equation

HRID 35679 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-6cf4e8aa67054fda944c45da66d14c6b
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04767780

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes