2-(2-Nitrophenyl)-4H-3,1-benzoxazin-4-one → 2-(2-Amino-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 1583741Notes

Reaction equation

HRID 1583741 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]=1)([O-])=O>C(OCC)(=O)C.[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]=1

Participants

4

Reactant 1

HCID 3476752-(2-Nitrophenyl)-4H-3,1-benzoxazin-4-one

Product 1

HCID 8383952-(2-Amino-phenyl)-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Nitrophenyl)-3,1-benzoxazin-4-one (1.1 g, 4.10 mmole) was suspended in 40 ml of ethyl acetate, with platinum oxide (100 mg) being added, and the resulting reaction mixture was hydrogenated at atmospheric pressure with vigorous stirring. After 3 hours, the catalyst was removed and the solvent was rotoevaporated. The residual yellow oil was subjected to flash chromatography to give a homogeneous product. Recrystallization from acetone provided the analytical sample, m.p. 163°-165° C. (lit.* 162° C.).

Workup

  1. additionbeing added
  2. customthe resulting reaction mixture
  3. customthe catalyst was removed
  4. customto give a homogeneous product
  5. customRecrystallization from acetone
  6. customprovided the analytical sample, m.p. 163°-165° C. (lit.* 162° C.)

Sources & evidence

ORD record
ord-93673244aa4948aeafe61369154663f8
Source dataset
uspto-grants-1985_11
Patent number
US04554272

Reaction notes

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