Sodium Hydroxide → 4-[(8-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 968680Notes

Reaction equation

C(=O)([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH:28]([CH3:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=3)(=[O:14])=[O:13])=[CH:8][CH:7]=1)OCC.[OH-].[Na+]>CO>[F:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:15]([S:12]([C:9]1[CH:8]=[CH:7][C:6]([OH:5])=[CH:11][CH:10]=1)(=[O:14])=[O:13])[CH:28]2[CH3:29]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of ethyl 4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenyl carbonate (0.45 g, 1.02 mmol) in methanol (5.0 mL) was treated with a 1 N sodium hydroxide (5.1 mL) solution, and heated at 75° C. for 14 hours. After cooling to room temperature, the methanol was evaporated in vacuo. The resulting aqueous mixture was acidified with a 1 N hydrochloric acid solution, diluted with a saturated, aqueous, sodium chloride solution (100 mL), and extracted with dichloromethane (5×15 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a white solid. The solid was purified by filtration through a short column of silica gel, eluting with ethyl acetate, to yield the title compound as a homogeneous, white, crystalline, solid (0.34 g, 89%), m.p. 188° C.; MS [(−ESI), m/z]: 368 [M−H]−;

Workup

temperatureAfter cooling to room temperature
customthe methanol was evaporated in vacuo
additiondiluted with a saturated, aqueous, sodium chloride solution (100 mL)
extractionextracted with dichloromethane (5×15 mL)
dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo to a white solid
filtrationThe solid was purified by filtration through a short column of silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-a3af07edb9954d95a28fa719c2a58726
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304073B2

Reaction notes

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