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

HRID 1534978Notes

Reaction equation

HRID 1534978 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.C1COCC1>[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

5

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-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 10% palladium on carbon (350 mg, 5% w/w) was added to a suspension of 7-nitro-3-oxo-3,4-dihydro-(2H)-1,4-benzoxazine (7 g, 39.3 mmol) in 50 ml of MeOH. The reaction mixture was hydrogenated at 40 psi for 16 hours. The reaction mixture was then diluted with THF (-200 mls) and the reaction was filtered through celite. The solvent was evaporated, leaving a brown solid as the residue. Product was recrystallized from THF/Hexane (1:5). Collected 4.2 g (72%) of a tan solid: m.p. 213-215, 'H NMR (300 M Hz, DMSO) δ 4.410 (S, 2H), 4.869 (S, 2H) 6.141 (d, 1H, J=2.44) 6.176 (dd, 1H, J=2.25, 4.69), 6.563 (d, 1H, J=8.19), 9.535 (brs, 1H); 13C NMR (300 MHz, DMSO) δ 66.9496, 102.2081, 108.1369, 116.5779; 116.8982, 144.5502, 145.4287, 164.389; Mass spectrum M+ at m/z 164

Workup

  1. filtrationthe reaction was filtered through celite
  2. customThe solvent was evaporated
  3. customleaving a brown solid as the residue
  4. customProduct was recrystallized from THF/Hexane (1:5)
  5. customCollected 4.2 g (72%) of a tan solid

Sources & evidence

ORD record
ord-9979459e974443418c7d735457bbdbcb
Source dataset
uspto-grants-1992_02
Patent number
US05091528

Reaction notes

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