Water → 5-aminoisoquinolin-1(2H)-one

HRID 420616Notes

Reaction equation

HRID 420616 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

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 addition in portions of 1.23 g of zinc powder (heating to 30 to 35° C.), it is stirred for two hours. The reaction mixture is suctioned off through a gas 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

Sources & evidence

ORD record
ord-069d005dad6045d090b647034b3d2be8
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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