2(3H)-Benzoxazolone, 6-nitro- → 6-amino-1,3-benzoxazol-2(3H)-one

HRID 843996Notes

Reaction equation

HRID 843996 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-])=O.[Sn]>Cl.O>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 784192(3H)-Benzoxazolone, 6-nitro-HCID 5352426Tin atom

Product 1

HCID 8269896-amino-1,3-benzoxazol-2(3H)-oneYield 35.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 6-Nitro-3H-benzooxazol-2-one (8.4 grams, 46.0 mmole) and Tin (16.0 g) in concentrated hydrochloric acid (100 ml) was stirred at 60° C. for 2 hours. The mixture was diluted with water, basified to pH 12 and extracted with ethyl acetate. The combined extracts were dried over Na2SO4, filtered, and concentrated to give an orange solid (2.45 g). MW 150; MS (m/e) 151 (M++1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e74c0e2095b94353a822c60138a48eb3
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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