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 589133Notes

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

Iron (91 mg, 1.6 mmol) was added to a mixture of 8-bromo-6-fluoro-5-nitro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-3-ol (121.0 mg, 0.3269 mmol) in acetic acid (3 mL), and heated overnight at 60° C. The mixture was extracted with ethyl acetate and the organic layer concentrated. Purification on silica gel eluting ethyl acetate in hexanes afforded product. LCMS calc. for C13H10BrFN3O (M+H)+: m/z=322.0. found: 322.0.

Workup

extractionThe mixture was extracted with ethyl acetate
concentrationthe organic layer concentrated
customPurification on silica gel
washeluting ethyl acetate in hexanes afforded product

Sources & evidence

ORD record: ord-295acf5134dc482b878aae6e9ddec568
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227985B2

Reaction notes

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