6-Fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one → 3-(4-Aminophenyl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

HRID 1271048Notes

Reaction equation

HRID 1271048 reaction equation
[F:1][C:2]1[C:3]([NH:22][CH3:23])=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1>C(O)C.[Pd]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[C:7](=[O:20])[C:6]3[CH:21]=[C:2]([F:1])[C:3]([NH:22][CH3:23])=[CH:4][C:5]=3[O:10][CH2:9]2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 184525156-Fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

Product 1

HCID 184524863-(4-Aminophenyl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-oneYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 6-fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.108 g, 0.33 mmol) in ethanol (6 mL) under Ar was added 10% Pd/C (0.04 g, 0.03 mmol Pd). The mixture was hydrogenated under 1 atm H2 overnight, filtered through Celite and concentrated to give 0.096 g (98%) of 3-(4-aminophenyl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one. RP-HPLC: 1.37 min; ES-MS (M+H)+=288.0; 1H-NMR (MeOH-d4) δ (ppm): 2.8 (s, 3 H), 5.5 (s, 2 H), 6.2 (d, 1 H), 7.2 (d, 2 H), 7.3 (d, 2 H), 7.4 (d, 1 H).

Workup

  1. customwas hydrogenated under 1 atm H2 overnight
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b6e8ba2b95314cccbc1a7de34c69e6b9
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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