Potassium Hydroxide → 7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 344967Notes

Reaction equation

HRID 344967 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15])=[O:4].[OH-].[K+]>CS(C)=O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][O:15][C:7]=2[CH:8]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 199683892-chloro-N-(2-hydroxy-4-nitrophenyl)acetamide

Product 1

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 8 (22 g) and powdered KOH (6.9 g) in DMSO (100 ml) was stirred at 95° C. for 30 min. and poured onto crushed ice (400 g). The resulting precipitate was collected and washed with H2O to give 9 (15.7 g, 85%): mp 230°-232° C.; MS m/e 194 (M+).

Workup

  1. additionpoured
  2. customThe resulting precipitate was collected
  3. washwashed with H2O

Sources & evidence

ORD record
ord-9da82c2c5dd74825809ab764a9740475
Source dataset
uspto-grants-1991_10
Patent number
US05055110

Reaction notes

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