7-methoxy-8-nitroisoquinolin-1(2H)-one → 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577488Notes

Reaction equation

HRID 577488 reaction equation
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[C:11]2[C:6]([CH:7]=[CH:8][NH:9][C:10]2=[O:16])=[CH:5][CH:4]=1>[Pd].C(O)C>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:16])[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 867237137-methoxy-8-nitroisoquinolin-1(2H)-one

Product 1

HCID 867237148-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 7-methoxy-8-nitroisoquinolin-1(2H)-one (296b, 30 g, 0.136 mol) and 10% palladium on carbon (15 g, 0.014 mol) in ethanol (1 L) was stirred at 40° C. under hydrogen (20 psi) for 72 hours. The mixture was filtered through celite, the flask and filter pad washed with ethanol (1 L), and the combined filtrates concentrated under vacuum to give 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (296c, 24 g, 92% yield) as a brown oil. MS: 193 [M+1].

Workup

  1. filtrationThe mixture was filtered through celite
  2. filtrationthe flask and filter pad
  3. washwashed with ethanol (1 L)
  4. concentrationthe combined filtrates concentrated under vacuum

Sources & evidence

ORD record
ord-340f148ea57746c49413a3ef3ac0ffbc
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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