Water → 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 2399331Notes

Reaction equation

HRID 2399331 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10](O)([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:9]([N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=[O:30])[C:8]=2[CH:31]=1)([O-:3])=[O:2].[H-].[Na+].O.C(OCC)(=O)C>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])=[C:9]([N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=[O:30])[C:8]=2[CH:31]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 193871146-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 193871336-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-nitro-2,2-dimethyl-3-hydroxy-3,4-dihydro-3-(trifluoroacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.5 g, 1.13 mmol) in tetrahydrofuran (20 ml) containing sodium hydride (80%, 0.034 g, 1.13 mol) was refluxed for one hour. Water and ethyl acetate were added to the cooled solution and the organic phase was separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (95/5), to give 0.13 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 189° C.

Workup

  1. temperaturewas refluxed for one hour
  2. customthe organic phase was separated
  3. customevaporated under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. washeluting with dichloromethane/acetone (95/5)

Sources & evidence

ORD record
ord-523755b69ab0494aa62934a5bd6838cf
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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