4-methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one → 8-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one

HRID 1687239Notes

Reaction equation

HRID 1687239 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:6]=2[O:5][CH2:4][CH2:3]1>[Pd].C(O)C>[NH2:14][C:12]1[CH:11]=[CH:10][C:7]2[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]=2[CH:13]=1

Participants

4

Reactant 1

HCID 672633784-methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one

Product 1

HCID 578538918-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-oneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Methyl-8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.16 g, 0.0072 mol) and 10% palladium on carbon in ethanol (70 mL) was hydrogenated. The reaction was filtered and evaporated. Purification by ISCO chromatography gave 8-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.027 g, 84%) as a tan solid. MP: 169-170° C.; 1H-NMR (DMSO-d6) δ 7.36 (d, 1H), 6.27-9 (d, 1H), 6.08 (s, 1H), 5.60 (s, 1H), 4.22-5 (m, 2H), 3.46-9 (m, 2H), 3.00 (s, 3H); LC/MS (ESI+): 193 (M+H).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated
  3. customPurification by ISCO chromatography

Sources & evidence

ORD record
ord-450aa017f16146a3acd2355f9ff63713
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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