Stannous chloride dihydrate → HCID 57438891, compound

HRID 557429Notes

Reaction equation

HRID 557429 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[C:8]([N+:13]([O-])=O)[CH:7]=[CH:6][C:5]=2[CH3:16].O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:13][C:8]1[CH:7]=[CH:6][C:5]([CH3:16])=[C:4]2[C:9]=1[C:10](=[O:12])[CH:11]=[C:2]([CH3:1])[O:3]2

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 574388902,8-Dimethyl-5-nitro-4H-1-benzopyran-4-one

Product 1

HCID 57438891HCID 57438891, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.78 g (8.12 mmol) of 2,8-dimethyl-5-nitro-4H-chromen-4-one (example 32, stage c) are heated with 9.16 g (40.6 mmol) of tin (II) chloride dihydrate in 70 ml of ethyl acetate at 70° C. overnight. After cooling to room temperature, the reaction mixture is adjusted to pH 9-10 with saturated sodium bicarbonate solution. After filtration through kieselguhr, the organic phase is separated off, and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution. After drying over sodium sulfate, the solvent is removed in vacuo. 1.5 g (99% of theory) of the title compound are obtained.

Workup

  1. filtrationAfter filtration through kieselguhr
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted several times with ethyl acetate
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3d5407f7b9294658a555e90b14795492
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

Loading…