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

HRID 2399312Notes

Reaction equation

HRID 2399312 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([CH3:16])[O:15][CH:9]3[C:8]=2[CH:17]=1)([O-:3])=[O:2].[NH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=[O:24].O.C(OCC)(=O)C>C(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]([CH3:16])([OH:15])[CH:9]([N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]3=[O:24])[C:8]=2[CH:17]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 88712-PyridoneHCID 157118886-nitro-2,2,3-trimethyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran

Product 1

HCID 221227126-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-3,4-dihydro-3-hydroxy-2H-1-benzopyranYield 25.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-nitro-2,2,3-trimethyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran (9.93 g, 0.0422 mol), 2(1H)-pyridinone (8.04 g, 0.0845 mol) and Triton B (40% in ethanol, 2.5 ml) in dioxan (100 ml) was heated at reflux for twenty hours. Water and ethyl acetate were added to the cooled solution, the organic phase separated and the solvent removed under reduced pressure. The residue was washed with diethyl ether and pentane, to give 3.53 g of 6-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-3,4-dihydro-3-hydroxy-2H-1-benzopyran, m.p. 214° C.

Workup

  1. temperatureat reflux for twenty hours
  2. customthe organic phase separated
  3. customthe solvent removed under reduced pressure
  4. washThe residue was washed with diethyl ether and pentane

Sources & evidence

ORD record
ord-e03e35491f6f4cf3839b9f475c12279c
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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