HCID 90410525, compound → HCID 90410261, compound

HRID 589055Notes

Reaction equation

[N:1]([C:4]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:5]=1[O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[CH2:9])=[N+]=[N-]>C1C=CC=CC=1>[N+:20]([C:19]1[C:4]2[N:1]3[CH2:9][C:8]3([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[CH2:7][O:6][C:5]=2[CH:16]=[CH:17][CH:18]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-{1-[(2-azido-3-nitrophenoxy)methyl]vinyl}pyridine (250 mg, 0.84 mmol) in benzene (15 mL) was refluxed at 80° C. for 15 h. The reaction was concentrated to give the crude product. The product was purified by FCC on silica gel eluting with a hexane:ethyl acetate gradient to give 7-nitro-1a-pyridin-2-yl-1a,2-dihydro-1H-azireno[2,1-c][1,4]benzoxazine as a solid (0.225 g, 90%). LCMS calculated for C14H12N3O3 (M+H)+: m/z=270.1. found: 270.1.

Workup

concentrationThe reaction was concentrated
customto give the crude product
customThe product was purified by FCC on silica gel eluting with a hexane

Sources & evidence

ORD record: ord-b892e6e8c3614f4f9ca84b4131df54cf
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227985B2

Reaction notes

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