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

HRID 975811Notes

Reaction equation

HRID 975811 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 10% palladium on carbon (0.24 g) and 2b (2.39 g, 12.3 mmol) in methanol (65 ml) was shaken under 25 lbs H2 in a Parr hydrogenation apparatus. After 3 h, the catalyst was filtered and the filtrate evaporated to afford 1.63 g (81%) of compound 2c. An analytical sample was recrystallization from MeOH/hexane. Mp 216°-7° C.

Workup

  1. filtrationthe catalyst was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-eeb9b0529dec444c8701a0665db6b2c1
Source dataset
uspto-grants-1997_03
Patent number
US05610158

Reaction notes

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