Ethyl Acetoacetate → HCID 23346132, compound

HRID 1856204Notes

Reaction equation

HRID 1856204 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:15]([F:18])([F:17])[F:16])([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9][CH2:8]2)[OH:4].[C:21](OCC)(=[O:26])[CH2:22][C:23]([CH3:25])=[O:24]>C1(C)C(C)=CC=CC=1>[F:17][C:15]([F:18])([F:16])[C:3]([C:2]([F:1])([F:19])[F:20])([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:21](=[O:26])[CH2:22][C:23](=[O:24])[CH3:25])[CH2:10][CH2:9][CH2:8]2)[OH:4]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 136265331,1,1,3,3,3-Hexafluoro-2-(1,2,3,4-tetrahydroquinolin-6-yl)propan-2-ol

Product 1

HCID 23346132HCID 23346132, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred mixture of 6.0 g (0.02 mole) of α,α-bis(trifluoromethyl)-1,2,3,4-tetrahydro-6-quinolinemethanol, 2.6 g (0.02 mole) of ethyl acetoacetate, and 100 ml of xylene is refluxed for 16 hours. The mixture is allowed to cool and is evaporated. The residue is triturated with a mixture of toluene, ethyl acetate, and hexane (60:10:30). The insoluble portion is filtered off, washed with water, and dried to give 1.6 g (23%) of α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-1,2,3,4-tetrahydro-6-quinolinemethanol. C. A solution of 10.5 g (0.027 mole) of α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-1,2,3,4-tetrahydro-6-quinolinemethanol in 30 ml of concentrated sulfuric acid is heated on a steam bath for 30-45 minutes, cooled to approximately 60° C., and poured into ice. When the ice is melted, the precipitate is filtered off, washed with water, and dried. The solid is recrystallized from 2-ethoxyethanol to give 7.2 g (74% ) of 2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-7-methyl-1H,5H-benzo[ij]quinolizin-5-one, m.p. 295°-296°.

Workup

  1. temperatureis refluxed for 16 hours
  2. temperatureto cool
  3. customis evaporated
  4. customThe residue is triturated with a mixture of toluene, ethyl acetate, and hexane (60:10:30)
  5. filtrationThe insoluble portion is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8d775d6a3956440796715b152c79fd7c
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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