7-Nitroisoquinoline → Isoquinolin-7-amine

HRID 2393566Notes

Reaction equation

HRID 2393566 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:13]=2)[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 1

HCID 122162777-Nitroisoquinoline

Product 1

HCID 14660277Isoquinolin-7-amineYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Nitroisoquinoline (1.62 g, 9.25 mmol) in ethanol (150 ml) was hydrogenated on a Paar Hydrogenator Apparatus over 5% palladium on carbon (0.2 g) as catalyst for 3 h at 50 psi The reaction mixture was filtered and the solvent removed at reduced pressure. Recrystallization of the solid from ethanol (3 ml) gave isoquinolin-7-amine (0.98 g) as a tan solid. MS 145 (M+H), NMR (CDCl3) 9.02 (s, 1H), 8.29 (d, 1H), 7.63 (d, 1H), 7.47 (d, 1H),7.13 (dd, H), 7.03 (d, 1H), 4.00 (broad, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed at reduced pressure
  3. customRecrystallization of the solid from ethanol (3 ml)

Sources & evidence

ORD record
ord-8b88f10116844d9899ff11e2ef08e4ef
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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