Potassium Carbonate → Ethyl 7-(4-acetonyl-1-piperazinyl)-6-fluoro-1-methyl-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate

HRID 1905430Notes

Reaction equation

HRID 1905430 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]1[CH:18]([CH3:20])[S:19][C:7]1=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2=[O:26].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35](=[O:37])[CH3:36]>CN(C)C=O>[CH2:34]([N:15]1[CH2:16][CH2:17][N:12]([C:11]2[CH:10]=[C:9]3[C:4]([C:5](=[O:26])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]4[S:19][CH:18]([CH3:20])[N:8]43)=[CH:3][C:2]=2[F:1])[CH2:13][CH2:14]1)[C:35]([CH3:36])=[O:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 10249018Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

Product 1

HCID 10002979Ethyl 7-(4-acetonyl-1-piperazinyl)-6-fluoro-1-methyl-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylateYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6-fluoro-1-methyl-7-(1-piperazinyl)-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate (3.8 g) was suspended in 50 ml of N,N-dimethylformamide, 1.66 g of potassium carbonate was added thereto, 1.65 g of bromoacetone was dropped in with ice cooling and stirring, and the mixture was stirred at room temperature for 20 hours. The reaction solution was poured over into ice water and the crystals separated out were collected by filtration, washed with water, dried and recrystallized from ethanol to give 3.7 g of desired compound in colorless powdery crystals, m.p. 196°-200° C. (decompn.).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. customthe crystals separated out
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-462c230f94fd418fb8cc10a9dffeec41
Source dataset
uspto-grants-1989_06
Patent number
US04843070

Reaction notes

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