Methylamine → ethyl 4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-3-methylamino-4-oxobutanoate

HRID 37121Notes

Reaction equation

HRID 37121 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][N:6]([C:8](=[O:16])[CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:4]=2[O:3]1.[CH3:25][NH2:26]>C(Cl)Cl.CO>[CH3:24][C:2]1([CH3:1])[CH2:7][N:6]([C:8](=[O:16])[CH:9]([NH:26][CH3:25])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 54151189ethyl 4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-4-oxo-2-butenoate

Product 1

HCID 19934602ethyl 4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-3-methylamino-4-oxobutanoateYield 36.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 3 ml of methylene chloride was dissolved 0.5 g of ethyl 4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-4-oxo-2-butenoate followed by addition of 0.116 g of methylamine in methanol. The mixture was stirred at room temperature for 4 days, at the end of which time the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and the resulting crude crystals were washed with ethanol-hexane to give 0.2 g of ethyl 4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-3-methylamino-4-oxobutanoate.

Workup

  1. distillationwas distilled off under reduced pressure
  2. customThe residue was purified by silica gel column chromatography
  3. washthe resulting crude crystals were washed with ethanol-hexane

Sources & evidence

ORD record
ord-df255d79e91940ec9590615c4828ca39
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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