8-bromo-6-fluoro-5-nitro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-3-ol → 8-Bromo-6-fluoro-3-pyridin-3-yl-2H-1,4-benzoxazin-5-amine

HRID 928554Notes

Reaction equation

[Br:1][C:2]1[C:11]2[O:10][CH2:9][C:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)(O)[NH:7][C:6]=2[C:5]([N+:19]([O-])=O)=[C:4]([F:22])[CH:3]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([F:22])[C:5]([NH2:19])=[C:6]2[C:11]=1[O:10][CH2:9][C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[N:7]2

Participants

Conditions

Temperature: 60 °C

Procedure

To 8-bromo-6-fluoro-5-nitro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-3-ol (690 mg, 1.9 mmol) in acetic acid (20 mL), iron (520 mg, 9.4 mmol) was added and heated at 60° C. overnight. The reaction was extracted with ethyl acetate to give the crude product, 0.60 g, 100%. 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.68 (m, 1H), 8.51 (m, 1H), 7.52 (m, 1H), 6.89 (m, 1H), 5.80 (s, 2H), 5.13 (s, 2H), 2.25 (s, 3H), 2.10 (s, 3H). LCMS calculated for C13H10BrFN3O (M+H)+: m/z=322.0, 324.0. found: 321.8, 323.8.

Workup

extractionThe reaction was extracted with ethyl acetate

Sources & evidence

ORD record: ord-111ba9350aaa42e0aa3c8e7bf5290cc7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290514B2

Reaction notes

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