Sodium Methoxide → Ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 1054214Notes

Reaction equation

HRID 1054214 reaction equation
[CH2:1]([O:8][N:9]([C:18]1[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=1[C:20]([O:22]CC)=O)[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([O:8][N:9]1[C:18]2[C:19](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:20]([OH:22])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]1=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 90258228ethyl 2-(N-(benzyloxy)-3-ethoxy-3-oxopropanamido)benzoate

Product 1

HCID 90258568Ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of ethyl 2-(N-(benzyloxy)-3-ethoxy-3-oxopropanamido)benzoate (1.3 g, 3.37 mmol) in MeOH (10 mL) was added sodium methoxide (0.255 g, 4.72 mmol) slowly at 20-25° C. Reaction mixture was stirred for 1 h. Excess methanol was distilled out and then reaction mixture diluted with NH4CJ solution. Precipitated product was filtered and dried to get titled compound in 58% yield.

Workup

  1. customReaction mixture
  2. distillationExcess methanol was distilled out
  3. customreaction mixture
  4. additiondiluted with NH4CJ solution
  5. filtrationPrecipitated product was filtered
  6. customdried

Sources & evidence

ORD record
ord-976db6fa065847e1b3de63088d106c2b
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

Loading…