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 2399320Notes

Reaction equation

HRID 2399320 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-02a472cae00649f29d0dd8226bffa9c1
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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