HCID 14770024, compound → 10-acetyl-4,5-dihydro-8-(m-fluorophenyl)7H-thieno[2,3-a]quinolizin-7-one

HRID 1109566Notes

Reaction equation

HRID 1109566 reaction equation
[OH-:1].[OH:2][C:3]1[N+:7]2[CH2:8][CH2:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]=2S[C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1>C1(C)C=CC=CC=1>[C:4]([C:15]1[CH:16]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:3](=[O:2])[N:7]2[C:6]=1[C:11]1[S:12][CH:13]=[CH:14][C:10]=1[CH2:9][CH2:8]2)(=[O:1])[CH3:3]

Participants

3

Reactant 1

HCID 14770024HCID 14770024, compound

Product 1

HCID 1902048310-acetyl-4,5-dihydro-8-(m-fluorophenyl)7H-thieno[2,3-a]quinolizin-7-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.303 g of 5,6-dihydro-3-hydroxy-2-(m-fluorophenyl )-thiazolo[3,2-a ]thieno[2,3-c ]pyridinium hydroxide (internal salt) and 0.145 ml of 3-butyl-2-one in 5 ml of toluene was heated under reflux for 1 hour. The solvent is evaporated in vacuo and the residue is chromatographed over silica gel with toluene/ethyl acetate (1:1). After recrystallization from ethanol, there was obtained 10-acetyl-4,5-dihydro-8-(m-fluorophenyl)7H-thieno[2,3-a]quinolizin-7-one of m.p. 109°110°.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is chromatographed over silica gel with toluene/ethyl acetate (1:1)
  4. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-1e5f5ca6d8c647288883f45dfc98dcfe
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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