Ethyl bromoacetate → 4-ethoxycarbonylmethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 2291766Notes

Reaction equation

HRID 2291766 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N+:8]([C:11]1[CH:21]=[CH:20][C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[CH:12]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:6]([O:5][C:3]([CH2:2][N:15]1[C:14]2[CH:20]=[CH:21][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][C:13]=2[O:18][CH2:17][C:16]1=[O:19])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 111501834-ethoxycarbonylmethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-oneYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl bromoacetate (18.4 g) was added dropwise at a temperature of 30° C. to 40° C. to a mixture of 7-nitro-2H-1,4-benzoxazin-3(4H)-one (19.4 g), potassium carbonate (15.2 g) and acetonitrile (100 ml), the mixture was refluxed under heating for 3 hours. When the reaction was completed, the liquor was filtered, the filtrate was distilled. Recrystallization of the resulting solid from toluene-hexane gave the desired 4-ethoxycarbonylmethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (20 g). mp. 120.5°-121.5° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. filtrationthe liquor was filtered
  4. distillationthe filtrate was distilled
  5. customRecrystallization of the resulting solid from toluene-hexane

Sources & evidence

ORD record
ord-59bbc318485c499daee91d5f32eef94f
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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