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

HRID 2399313Notes

Reaction equation

HRID 2399313 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])(O)[CH:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=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]([CH3:14])([CH3:13])[C:10]([CH3:16])=[C:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 221227126-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-3,4-dihydro-3-hydroxy-2H-1-benzopyran

Product 1

HCID 221228176-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-3,4-dihydro-3-hydroxy-2H-1-benzopyran (3.53 g, 0.0107 mol) in tetrahydrofuran (150 ml) was treated with sodium hydride (80%, 0.32 g). The mixture was heated at reflux for sixteen hours. Water and ethyl acetate were added to the cooled solution and the organic layer separated, dried and evaporated under reduced pressure to afford 1.62 g of 6-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 200° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for sixteen hours
  3. customthe organic layer separated
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-60b0775bca8844ecbab8cacabd345b70
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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