Sodium Carbonate → 4,6-Dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acid

HRID 2379580Notes

Reaction equation

HRID 2379580 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH:4]=[C:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.[Pd]>[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([OH:17])=[O:16])[CH:4]=[C:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 18957067Benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

Product 1

HCID 156408234,6-Dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 3.88 g of benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate in 140 ml of ethanol was treated with 0.78 g of 10 percent palladium/carbon, whereupon the mixture was hydrogenated for 16 hours. The reaction mixture was diluted with 1,400 ml of water and treated with 4.18 g of sodium carbonate. The catalyst was filtered off and the filtrate was acidified with 25 percent hydrochloric acid. The separated crystals were filtered off under suction, washed with water and dried in a vacuum. There was obtained 2.85 g of 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylic acid as white crystals with a m.p. of 295° (decomposition).

Workup

  1. filtrationThe catalyst was filtered off
  2. filtrationThe separated crystals were filtered off under suction
  3. washwashed with water
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-270f524c4f7747da8c6ce3d3df77bb79
Source dataset
uspto-grants-1994_11
Patent number
US05362738

Reaction notes

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