4-Benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester → 4-Hydroxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester

HRID 2253184Notes

Reaction equation

HRID 2253184 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]2[C:16]([C:17]=1[O:18]CC1C=CC=CC=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]>[Pd].CCOC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 667129544-Benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667127644-Hydroxy-1-methoxy-isoquinoline-3-carboxylic acid butyl esterYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester (164 mg, 0.45 mmol), Pd/C (50 mg, 10 wt % Pd) and EtOAc (15 ml) was stirred under a H2-atmosphere at ambient pressure and temperature for 16 h. Then the mixture was filtered through a pad of celite. Celite and filter cake were washed thoroughly with EtOAc and the combined organic phases were concentrated in vacuo to give the title compound as a white solid (115 mg); 1H NMR (CDCl3): δ=11.48 (s, 1H), 8.27 to 8.32 (m, 1H), 8.17 to 8.21 (m, 1H), 7.65 to 7.78 (m, 2H), 4.43 (t, 2H), 4.10 (s, 3H), 1.87 (m, 2H), 1.54 (m, 2H), 1.02 (t, 3H).

Workup

  1. filtrationThen the mixture was filtered through a pad of celite
  2. filtrationCelite and filter cake
  3. washwere washed thoroughly with EtOAc
  4. concentrationthe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-d7cb6ca412744b2c98dbc06abfd7664d
Source dataset
uspto-grants-2008_01
Patent number
US07323475B2

Reaction notes

Loading…