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

HRID 1844007Notes

Reaction equation

HRID 1844007 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 85.71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Using analogous reaction conditions, work up and purification as described for the preparation of intermediate I-24c above, 7-Nitro-3,4-dihydro-2H-isoquinolin-1-one (I-24a: 2.5 g, 0.013 mol) in methanol (50 mL) was reacted with 10% Pd—C (0.5 g) to afford the crude product, which was washed with n-hexane to afford 1.8 g of the product (85.71% yield).

Workup

  1. customreaction conditions
  2. custompurification
  3. customas described for the preparation of intermediate I-24c above
  4. customto afford the crude product, which
  5. washwas washed with n-hexane

Sources & evidence

ORD record
ord-0702975ce5d046edbc423eebbc941aee
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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