Water → 5-aminoisoquinolin-1(2H)-one

HRID 2182731Notes

Reaction equation

HRID 2182731 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][NH:8][C:9]2=[O:14])([O-])=O.[Cl-].[NH4+].O>C(O)C.O1CCCC1.[Zn]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][NH:8][C:9]2=[O:14]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2313785-Nitro-1,2-dihydroisoquinolin-1-one

Product 1

HCID 20725-aminoisoquinolin-1(2H)-oneYield 88.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
32.5 °C

Procedure

268.3 mg (1.51 mmol) of 5-nitroisoquinolin-1(2H)-one is added with 376.5 mg of ammonium chloride and 2.6 ml of water in 14 ml of ethanol and 5.4 ml of tetrahydrofuran. After the addition of 1.23 g of zinc powder in portions (heating to 30 to 35° C.), it is stirred for two hours. The reaction mixture is suctioned off via a glass fiber filter and rewashed with ethyl acetate. After the filtrate is washed with water and saturated sodium chloride solution, the organic phase is dried as usual. Filtering off the desiccant and spinning-off the solvent produce 196.5 mg (88.1%) of the desired amine.

Workup

  1. filtrationfilter
  2. washAfter the filtrate is washed with water and saturated sodium chloride solution
  3. customthe organic phase is dried as usual
  4. filtrationFiltering off the desiccant and spinning-off the solvent

Sources & evidence

ORD record
ord-197c89d72fca488884ef6ab628dab446
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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