Dimethylformamide → 8-Amino-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

HRID 1040928Notes

Reaction equation

HRID 1040928 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[NH:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-])=O.CN(C=O)C>[Pd].C(O)C>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[NH:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 578537818-nitro-3,4-dihydro-2H-1,4-benzoxazepin-5-one

Product 1

HCID 578538478-Amino-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-oneYield 35.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.23 g, 0.00096 mol), 10% palladium on carbon (0.02 g), DMF (10 mL), and ethanol (30 mL) was hydrogenated for 3 days. Filtration and evaporation gave an oil which was chromatographed on Al2O3 to give 8-amino-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.06 g, 35%) as a tan solid. MP: 151-2° C.; 1H-NMR (DMSO-d6) δ 7.77 (s, 1H), 7.54-6 (d, 1H), 6.25-7 (d, 1H), 6.05 (s, 1H), 5.63 (s, 2H), 4.17-9 (m, 2H), 3.25-8 (m, 2H); LC/MS (ESI+): 179 (M+H).

Workup

  1. filtrationFiltration and evaporation
  2. customgave an oil which
  3. customwas chromatographed on Al2O3

Sources & evidence

ORD record
ord-1c9b1645b0834594bc4b34aeacbaf47f
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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