Ethanol → 4-Hydroxy-7-phenethyl-isoquinoline-3-carboxylic acid methyl ester

HRID 1481135Notes

Reaction equation

HRID 1481135 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]=2)=[O:4].CCO>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]=2)=[O:4]

Participants

5

Reactant 2

HCID 702EthanolHCID 89812978HCID 89812978, compound

Product 1

HCID 898128624-Hydroxy-7-phenethyl-isoquinoline-3-carboxylic acid methyl esterYield 569.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxy-7-phenylethynyl-isoquinoline-3-carboxylic acid methyl ester (60 mg, 0.20 mmol), 10% Pd/C (200 mg), EtOH (10 mL) and EtOAc (20 mL) was stirred under H2 atmosphere for 48 h. The resulting mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (0-40% EtOAc/hexanes) to give 350 mg of the title compound. MS: (+) m/z 308.26 (M+1).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1d619125794c498e8fc1f61b0fa699a2
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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