Hydrochloric Acid → 8-Fluoro-10-hydroxy-10,11-dihydrodibenzo[b,f]thiepin-3-carboxylic Acid

HRID 485470Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[CH2:8][C:7](=[O:19])[C:6]=2[CH:20]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+].Cl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[CH2:8][CH:7]([OH:19])[C:6]=2[CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Suspend 15.5 gm of the crude 10-keto compound of Step B in 750 ml of water and add 10 gm of sodium bicarbonate. Stir the mixture and warm to 50° C. for 15-20 minutes. Stop heating and slowly add 5 gm of sodium borohydride. Acidify the mixture with 10% aqueous hydrochloric acid, separate the solids by filtration, wash with water and air-dry. The residue may be used as such in the next step. (m.p. 204°-210° C., subsequent gassing)

Workup

temperatureStop heating
customseparate the solids
filtrationby filtration
washwash with water
customair-dry

Sources & evidence

ORD record: ord-4938c9c22f6b40ccb63fe12a658b6011
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04536507

Reaction notes

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