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

HRID 346476

反応式

HRID 346476 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-0cc37b0f01c14e7797475ffa60949e5f
出典データセット
uspto-grants-2007_02
特許番号
US07173022B2

関連ノート

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