Stannous chloride dihydrate → 5-amino-2-benzylisoquinolin-1(2H)-one

HRID 749209Notes

Reaction equation

HRID 749209 reaction equation
O.O.[Sn](Cl)Cl.[CH2:6]([N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[N+:23]([O-])=O)[C:14]1=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:23][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[CH:22][N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:14]2=[O:26]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 184445282-benzyl-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 184445335-amino-2-benzylisoquinolin-1(2H)-oneYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tin(II) chloride dihydrate (1.21 g, 5.36 mmol) was added to a stirred solution of 2-benzyl-5-nitroisoquinolin-1(2H)-one (300 mg, 1.07 mmol) in anhydrous ethanol (20 mL). The reaction mixture was stirred at reflux for 20 h. The resulting mixture was cooled to room temperature, treated with saturated aqueous sodium bicarbonate to pH=11 and diluted with water (100 mL). The obtained mixture was extracted with ethyl acetate (3×70 mL). The combined organic fractions were dried over anhydrous Na2SO4, filtered and evaporated to give 5-amino-2-benzylisoquinolin-1(2H)-one (248 mg, 1.0 mmol, 93% yield) as an orange foam.

Workup

  1. temperatureat reflux for 20 h
  2. extractionThe obtained mixture was extracted with ethyl acetate (3×70 mL)
  3. dry with materialThe combined organic fractions were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d50aa7129329405187ee1311c434aeaa
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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