Hydrochloric Acid → 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 346476

반응식

HRID 346476 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:4]=1.Cl>C(O)C.[Pd]>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:4]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 21069882(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride

생성물 1

HCID 210698804-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile수율 99%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride): Intermediate 1,4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile, (2.46 g, 13.13 mmol) was dissolved in hot ethanol (150 mL). Aqueous 1N HCl (15 mL) was added followed by 10% Pd/C (200 mg). The mixture was shaken under H2 (55 psi) for 4 h., then filtered through Celite and concentrated in vacuo. The remaining residue was partitioned between ethyl acetate and water. The aqueous layer was isolated and lyophilized to give the title compound as a white powder (2.96 g, 99% yield). 1H NMR (500 MHz, CD3OD) δ ppm: 9.51 (1H, s), 8.63 (1H, s), 7.85 (1H, dd, J=8.5, 5.8 Hz), 7.68 (1H, dd, J=8.8, 2.4 Hz), 7.49 (1H, td, J=8.3, 2.4 Hz), 4.20 (2H, s). LCMS (M+H) calcd for C9H10N4F: 193.08; found: 193.16.

후처리

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe remaining residue was partitioned between ethyl acetate and water
  4. customThe aqueous layer was isolated

출처 및 근거

ORD 기록
ord-0cc37b0f01c14e7797475ffa60949e5f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173022B2

연결된 노트

불러오는 중…