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

HRID 1655382Notes

Reaction equation

HRID 1655382 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]3([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[O:15][CH:9]3[C:8]=2[CH:24]=1)([O-:3])=[O:2].[NH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]1=[O:31].O.C(OCC)(=O)C>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])([OH:15])[CH:9]([N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]3=[O:31])[C:8]=2[CH:24]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 88712-PyridoneHCID 19386922HCID 19386922, compound

Product 1

HCID 193871146-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 19.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran (0.4 g, 1.16 mmol), 2(1H)-pyridinone (0.22 g, 2.32 mmol) and Triton B (0.05 ml) in dioxane (3 ml) was heated at reflux for nineteen hours. Water and ethyl acetate were added, and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (95/5), to give 0.1 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 158° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for nineteen hours
  3. customthe organic phase separated
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with dichloromethane/acetone (95/5)

Sources & evidence

ORD record
ord-be12cd43a17744c191a19a68d3979524
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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