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

HRID 417921Notes

Reaction equation

HRID 417921 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.CO>[Pd].CCOC(C)=O>[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 2

HCID 887MethanolHCID 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 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-Nitro-4H-benzo[1,4]oxazin-3-one (0.65 g, 3.3 mmol) and 10% palladium on carbon (0.13 g) were combined in EtOAc (15 mL) and MeOH (15 mL) and hydrogenated for 2 h at atmospheric pressure. The catalyst was removed by filtration through celite and the filtrate reduced in vacuo to yield the title compound as a colourless oil (0.50 g, 91%). δH (DMSO-d6) 4.42 (2H, s), 4.89 (2H, br s), 6.13-6.20 (2H, m), 6.56 (1H, d, J 8.1 Hz), 10.27 (1H, br s).

Workup

  1. customThe catalyst was removed by filtration through celite

Sources & evidence

ORD record
ord-dbf68fd6059442cc92254761fb481355
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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