Water → 5-amino-1H-isochromen-1-one

HRID 1161179Notes

Reaction equation

HRID 1161179 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][O:13][C:14]2=[O:19])([O-])=O.C(=O)(O)[O-].[Na+].O>C1COCC1.CCOC(C)=O>[NH2:6][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][O:13][C:14]2=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 100806665-amino-1H-isochromen-1-oneYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tin(II)chloride dihydrate (41.9 g, 185.7 mmol) was added to a stirred solution of 5-nitro-1H-isochromen-1-one (7.1 g, 37.1 mmol) in anhydrous THF (120 mL). The reaction mixture was stirred at room temperature for 18 h. The resulting mixture was diluted with EtOAc (400 mL) and treated with saturated aqueous sodium bicarbonate to pH=10. Water (100 mL) was added and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×150 mL) and the combined organic fractions were dried over Na2SO4, filtered and evaporated to yield 5-amino-1H-isochromen-1-one (5.8 g, 36.0 mmol, 97%) as a yellow solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×150 mL)
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ecf14b7042cc49479920f0d096380d6c
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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