Water → Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907949Notes

Reaction equation

HRID 907949 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:24][CH:23]=1)=O.[O-:33][CH2:34][CH3:35].[Na+].O>C(OCC)(=O)CC.CCOC(C)=O>[CH3:29][N:28]([CH3:30])[C:26]([C:25]1[CH:31]=[CH:32][C:22]([CH:20]2[C:34](=[O:33])[C:35]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][CH:6]2[C:5]2[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:23][CH:24]=1)=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 105592054-formyl-N,N-dimethylbenzamideHCID 178519076HCID 178519076, compound

Product 1

HCID 67261670Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 44%

Reagents, catalysts & solvents 2

HCID 7749Ethyl PropionateSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

Sodium (115 mg, 5 mmol) was added to EtOH (10 mL) to afford sodium ethoxide. (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.96 mmol) and 4-formyl-N,N-dimethylbenzamide (382 mg, 2.16 mmol) were dissolved in ethyl propionate (10 mL), and the sodium ethoxide solution was added dropwise to the mixture at 0° C., then the mixture were heated to 30° C. for 1 h. To the reaction mixture was added water and EtOAc, the organic phase was separated, washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and then concentrated to afford the crude product. The crude product was purified by flash chromatography (MeOH:DCM 1:25) to give the title compound (400 mg, yield 44%). LC-MS (ESI) m/z: 461(M+1)+.

Workup

  1. customthe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customThe crude product was purified by flash chromatography (MeOH:DCM 1:25)

Sources & evidence

ORD record
ord-39ca926ed09b49d1a052cebabf822a1d
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

Loading…