Sodium Hydroxide → trans-4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-4-oxo-2-butenoic acid

HRID 37112Notes

Reaction equation

HRID 37112 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]CC)=[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.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:24])[CH2:7][N:6]([C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]([OH:13])=[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15291770HCID 15291770, compound

Product 1

HCID 15291774trans-4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-4-oxo-2-butenoic acidYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2 ml of ethanol was dissolved 0.5 g of ethyl trans-4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4yl)-4-oxo-2-butenoate followed by addition of 1.5ml of an aqueous solution of 0.06 g of sodium hydroxide. The mixture was stirred at room temperature for 2 hours. The ethanol was distilled off under reduced pressure and the residue was adjusted to pH 4 with 1N hydrochloric acid. The resulting precipitate was recovered by filtration and washed with water and ethanol to give 0.31 g of trans-4-(3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-4-yl)-4-oxo-2-butenoic acid.

Workup

  1. distillationThe ethanol was distilled off under reduced pressure
  2. filtrationThe resulting precipitate was recovered by filtration
  3. washwashed with water and ethanol

Sources & evidence

ORD record
ord-d9e3a7d1e281459aab62c43c99b56906
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

Loading…