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

HRID 1655375Notes

Reaction equation

HRID 1655375 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-4d900dd5ffd441cc88624cd07e02aeb7
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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