Methanol → 2-(2,3-dihydrobenzofuran-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

HRID 750157Notes

Reaction equation

HRID 750157 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]3[O:21][CH2:20][CH2:19][C:18]=3[CH:22]=1)[C:6]([C:23]([OH:25])=[O:24])=[C:5]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CO.[H][H]>[C].[Pd].C1COCC1>[O:21]1[C:17]2[CH:16]=[CH:15][C:14]([CH2:13][N:7]3[C:6]([C:23]([OH:25])=[O:24])=[C:5]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:4]4[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=4)[C:8]3=[O:12])=[CH:22][C:18]=2[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 887MethanolHCID 230608896-bromo-2-(2,3-dihydrobenzofuran-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 230609682-(2,3-dihydrobenzofuran-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic AcidYield 65.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-2-(2,3-dihydrobenzofuran-5-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (350 mg), 10% palladium carbon (150 mg), methanol (5 ml) and THF (5 ml) was stirred at room temperature under 1 atm hydrogen pressure for 12 hrs. Palladium carbon was filtered off, and the filtrate was concentrated. The obtained crystals were washed with diethyl ether to give the title compound (190 mg).

Workup

  1. filtrationPalladium carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. washThe obtained crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-df7102cfa49c4d75aef0e7194ca9c4c2
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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