Ammonia → 1-Amino-7-isoquinolinemethanamine

HRID 2304300Notes

Reaction equation

HRID 2304300 reaction equation
N.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.[H][H]>CO.[Ni]>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][NH2:14])[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 226658481-Aminoisoquinoline-7-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 226658411-Amino-7-isoquinolinemethanamineYield 25.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Liquid ammonia (210 mL) was added to a mixture of 4.2 g of 1-amino-isoquinoline-7-carbonitrile and 4.0 g of Raney-Ni in 210 mL of methanol in a steel vessel Hydrogen was pressed upon until an initial pressure of 100 atm. was obtained. This mixture was reacted for 16 hours at ambient temperature, the catalyst subsequently removed by filtration and the solvent pumped off. The residue was purified by silica chromatography (methanol/ammonia saturated methanol=85:15, 8:2) yielding 1.1 g (25%) of the title compound as a light yellow solid. M.p. 114-117° C.

Workup

  1. customwas obtained
  2. customThis mixture was reacted for 16 hours at ambient temperature
  3. customthe catalyst subsequently removed by filtration
  4. customThe residue was purified by silica chromatography (methanol/ammonia saturated methanol=85:15, 8:2)

Sources & evidence

ORD record
ord-532db6843d4949a29d188bcff86de99a
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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