Water → 7-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1638831Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1.[CH2:18](Br)[C:19]#[CH:20].O>CN(C)C=O>[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[N:8]([CH2:20][C:19]#[CH:18])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of sodium hydride (0.06 g) in N,N-dimethylformamide (3 ml) was cooled to 0° C. 7-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (0.57 g) was added thereto at 0° to 5° C., and the resultant mixture was stirred for 30 minutes. Propargyl bromide (0.35 g) was added to the mixture, which was gradually heated to room temperature, and the reaction was continued for 6 hours. After addition of water, the resultant mixture was extracted with ethyl acetate, and the extract was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and n-hexane (1:1) as an eluent to give 7-fluoro-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.47 g). m.p., 109.1° C.

Workup

temperaturewas gradually heated to room temperature
extractionthe resultant mixture was extracted with ethyl acetate
washthe extract was washed with water
customdried
concentrationconcentrated
customThe residue was purified by silica gel thin layer chromatography
additiona mixture of ethyl acetate and n-hexane (1:1) as an eluent

Sources & evidence

ORD record: ord-891f062035cf49b59860a3d79619b77d
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04880925

Reaction notes

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