HCID 59536308, compound → HCID 42611254, compound

HRID 445241Notes

Reaction equation

HRID 445241 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][CH:4]=1>CCO.[Pd]>[CH3:1][N:2]([CH3:24])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 59536308HCID 59536308, compound

Product 1

HCID 42611254HCID 42611254, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 1-(4-(dimethylamino)phenyl)isoquinoline-2(1H)-carboxylate (79 mg, 0.24 mmol) in EtOH (4 mL) was stirred with 10% Pd/C (0.062 g, 0.58 mmol) under hydrogen atmosphere at RT for 14 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated in vacuo. The crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes) to provide the title compound as a clear oil. MS (ESI pos. ion) m/z: 325 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c1c9bf4303a54ad58f3ca0f8c2cf6482
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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