1,3-Thiazole-5-carbaldehyde → Methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907852Notes

Reaction equation

HRID 907852 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[CH:8](=[N:15]/[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][O:19][C:20]2=[O:25])\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:26][O-:27].[Na+]>C(OCC)(=O)CC>[O:27]=[C:26]1[C:17]2[C:21]([C:20]([O:19][CH3:18])=[O:25])=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]1[C:5]1[S:1][CH:2]=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 27735771,3-Thiazole-5-carbaldehydeHCID 10942334Sodium MethoxideHCID 178519069HCID 178519069, compound

Product 1

HCID 67258775Methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 7.5%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

A mixture of thiazole-5-carbaldehyde (500 mg, 4 mmol), (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (960 mg, 4 mmol), sodium methanolate (375 mg, 16.1 mmol) and ethyl propionate (30 mL) were stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (4×100 mL) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 10:1 to 1:1) to give methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (110 mg, yield 7%). LC-MS (ESI) m/z: 379 (M+1)+.

Workup

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (4×100 mL)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 10:1 to 1:1)

Sources & evidence

ORD record
ord-d05fe45c92814e21b1d934e97957fe49
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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