Water → 6-nitro-2,2-dimethyl-3-(N-methyl-N-hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 2399322Notes

Reaction equation

HRID 2399322 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15]Br)=[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].Cl.[CH3:26][NH:27][OH:28].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][N:27]([CH3:26])[OH:28])=[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 11430Potassium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 193872966-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 193870396-nitro-2,2-dimethyl-3-(N-methyl-N-hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 6.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.30 g, 7.7 mmol), N-methylhydroxylamine hydrochloride (0.64 g, 7.7 mmol) and potassium carbonate (0.97 g, 7.7 mmol) in ethanol (10 ml) was heated at reflux for 30 minutes. Water was added and the mixture extracted with dichloromethane. The organic phase was separated and the solvent evaporated under reduced pressure. The residue was washed with diethyl ether, affording 0.19 g of 6-nitro-2,2-dimethyl-3-(N-methyl-N-hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 159° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. extractionthe mixture extracted with dichloromethane
  4. customThe organic phase was separated
  5. customthe solvent evaporated under reduced pressure
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-652b51ef03b443c4a71f6af7130c68fb
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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