Methylamine → 6-nitro-2,2-dimethyl-3-(methylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 2399321Notes

Reaction equation

HRID 2399321 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].[CH3:25][NH2:26]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][NH:26][CH3:25])=[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

4

Reactant 2

HCID 6329MethylamineHCID 193872966-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 193870896-nitro-2,2-dimethyl-3-(methylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.5 g, 1.27 mmol) and methylamine (40% in water, 1.1 ml, 1.397 mmol) in methanol (12 ml) was stirred at room temperature during four hours. The solvents were evaporated under reduced pressure, and water and ethyl acetate added to the residue. After stirring, the organic phase was separated and evaporated under reduced pressure. The residue was dissolved in diethyl ether and precipitated with pentane, to give 0.31 g of 6-nitro-2,2-dimethyl-3-(methylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 128° C.

Workup

  1. customThe solvents were evaporated under reduced pressure, and water and ethyl acetate
  2. additionadded to the residue
  3. customthe organic phase was separated
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in diethyl ether
  6. customprecipitated with pentane

Sources & evidence

ORD record
ord-f77514c7f01343119109ce0e80783b77
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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