Triethylamine → Isoquinolin-8-amine

HRID 880499Notes

Reaction equation

HRID 880499 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(N(CC)CC)C>CN(C)C=O.[Pd]>[CH:7]1[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][C:9]=2[NH2:12])[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 8169835-Bromo-8-nitroisoquinoline

Product 1

HCID 13927912Isoquinolin-8-amineYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-bromo-8-nitro-isoquinoline (2.0 g, 7.93 mmol), triethylamine (1.2 g, 11.90 mmol) and Pd/C (10%; 200 mg) in dimethylformamide (10 mL) was hydrogenated at atmospheric pressure for 2 h. The reaction mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford isoquinolin-8-amine (700 mg, 66%) as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d13f8bea20864cf1871ff918fcc4a877
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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