Hydrogen Bromide → 4.7-Dihydroxy-8-methyl-3-(3-fluorophenylcarbamoyl)coumarin

HRID 55332Notes

Reaction equation

C([O:8][C:9]1[C:18]([CH3:19])=[C:17]2[C:12]([C:13]([OH:31])=[C:14]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:15](=[O:20])[O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Br.O>C(O)(=O)C>[OH:31][C:13]1[C:12]2[C:17](=[C:18]([CH3:19])[C:9]([OH:8])=[CH:10][CH:11]=2)[O:16][C:15](=[O:20])[C:14]=1[C:21](=[O:30])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the compound of Step A (471 mg, 1.12 mmol) in acetic acid (10 ml) was added hydrobromic acid (48%, 5 ml). The mixture was refluxed at 100° C. for 18 hours. After cooling to room temperature, the reaction mixture was poured into water and a precipitate formed. After filtration, the solid was washed with water and then crystallized from dioxane-methanol. The title product was obtained as a white crystalline solid, mp 287°-289° C., (94.9 mg, 0.307 mmol, yield 27.4%). Analysis: Calculated for C17H12NO5F: C, 62.01 ; H, 3.65; N, 4.26. Found: C, 6204; H, 3.65; N, 4.34. 1H NMR (DMSO-d6): 7.74 (d, J=8.70 Hz, 1H), 7.65 (d, J=11.3 Hz, 1H), 7.43 (m, 1H), 7.40 (m, 1H), 7.04 (m, 1H), 6.98 (d, J=8.70 Hz, 1H), 2.26 (s, 3H).

Workup

temperatureAfter cooling to room temperature
customa precipitate formed
filtrationAfter filtration
washthe solid was washed with water
customcrystallized from dioxane-methanol

Sources & evidence

ORD record: ord-ba3e63a32cef4e7db3c4cdf0799e3b5d
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624951

Reaction notes

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