Water → 5-amino-1H-isochromen-1-one

HRID 418470Notes

Reaction equation

HRID 418470 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>O1CCCC1.C(OCC)(=O)C>[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 tetrahydrofuran (120 mL). The reaction mixture was stirred at room temperature for 18 h. The resulting mixture was diluted with ethyl acetate (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 sodium sulfate, 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 sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6856d543c1144559aca3ede37f780e37
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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