Hydrochloric Acid → (Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

HRID 2371477Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH:22]=[N:23][OH:24].B.N1C=CC=CC=1.Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][NH:23][OH:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of the oxime from Step 3 (2.0 g, 5.9 mmol) in ethanol (35 mL) at 0° C. there was added pyridine-borane (1.1 g, 11.8 mmol) and 12N aqueous HCl (1.48 mL, 17.75 mmol). The mixture was stirred at 0° C. for 1 hour, then warmed to room temperature. Most of the ethanol was evaporated, the residue diluted with water and ethyl acetate (the product as hydrochloride salt remains in the organic phase) and basified with 1N aqueous NaOH. The product obtained from the organic phase was triturated with hexane and filtered to afford the title compound as a yellow solid, mp: 126° C. dec.

Workup

temperaturewarmed to room temperature
customMost of the ethanol was evaporated
additionthe residue diluted with water and ethyl acetate (the product as hydrochloride salt
customThe product obtained from the organic phase
customwas triturated with hexane
filtrationfiltered

Sources & evidence

ORD record: ord-1767a2ddce024bb1aec799fa9bbda00f
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05093356

Reaction notes

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