7-Nitroisoquinoline → Isoquinolin-7-amine

HRID 1953560Notes

Reaction equation

HRID 1953560 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-5c09a0f9855b407b9d5e41a5696af3bb
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

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