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

HRID 379622노트

반응식

HRID 379622 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2723995Borane;pyridineHCID 86745521(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-(2-hydroximinoethyl)indene

생성물 1

HCID 86745522(Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

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 12 N 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 was diluted with water and ethyl acetate (the product as hydrochloride salt remains in the organic phase) and was basified with 1N aqueous NaOH. The product obtained from the organic phase was triturated with hexane and was filtered to afford the title compound as a yellow solid, mp: 126° C. dec.

후처리

  1. temperaturewarmed to room temperature
  2. customMost of the ethanol was evaporated
  3. additionthe residue was diluted with water and ethyl acetate (the product as hydrochloride salt
  4. customThe product obtained from the organic phase
  5. customwas triturated with hexane
  6. filtrationwas filtered

출처 및 근거

ORD 기록
ord-93e3427ce74c47a592fbde01f8075513
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

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