7-Nitro-3,4-dihydroisoquinolin-1(2H)-one → 7-Amino-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 2042122Notes

Reaction equation

HRID 2042122 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 131528447-Amino-1,2,3,4-tetrahydroisoquinolin-1-oneYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 7-nitro-3,4-dihydro-2H-isoquinolin-1-one (11.6 g, 60 mmol) and 10% Pd/C (1.2 g) in MeOH was stirred overnight at RT under H2 (40 psi). The mixture was filtered through Celite® and washed with MeOH. The filtrate was evaporated under vacuum to afford 8.2 g of 7-amino-3,4-dihydro-2H-isoquinolin-1-one, which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with MeOH
  3. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-58b0597ed2c542fdbb537b2cb01ed448
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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