Methanol → HCID 69157076, compound

HRID 750155Notes

Reaction equation

HRID 750155 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].CO.[H][H]>[C].[Pd].C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 10239063HCID 10239063, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69157076HCID 69157076, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-benzo[1,3]dioxol-5-ylmethyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), 10% palladium carbon (300 mg), methanol (6 ml) and THF (6 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 residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized (ethyl acetate-hexane) to give the title compound (230 mg).

Workup

  1. filtrationPalladium carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  4. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6c90fd2a94f947228e7f33d246a84403
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…