Hydrazine hydrate (1:1) → 4-Chloro-6-methyl-1H-pyrazolo[4,3-c]pyridine

HRID 69312ノート

反応式

HRID 69312 の反応式
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6](Cl)[CH:5]=[C:4]([CH3:11])[N:3]=1.O.[NH2:13][NH2:14]>ClCCCl>[Cl:1][C:2]1[C:7]2[CH:8]=[N:13][NH:14][C:6]=2[CH:5]=[C:4]([CH3:11])[N:3]=1

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 112524812,4-Dichloro-6-methylnicotinaldehyde

生成物 1

HCID 730127754-Chloro-6-methyl-1H-pyrazolo[4,3-c]pyridine

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2,4-dichloro-6-methylpyridine-3-carbaldehyde (12 g, 63 mmol) in 1,2-dichloroethane (200 mL) was added hydrazine monohydrate (9.52 g, 0.190 mol), and the reaction mixture was heated at 80° C. for 18 hours. After removal of solvents in vacuo, the residue was suspended in water (150 mL) and stirred for 30 minutes. The resulting precipitate was collected by filtration and washed with petroleum ether (2×250 mL), then was suspended in chloroform (150 mL), stirred for 30 minutes and filtered. The chloroform suspension was repeated twice to afford the product as a white solid. Yield: 6.7 g, 40 mmol, 63%. LCMS m/z 168.1 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 13.70 (br s, 1H), 8.21 (s, 1H), 7.38 (s, 1H), 2.52 (s, 3H).

後処理

  1. customAfter removal of solvents in vacuo
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with petroleum ether (2×250 mL)
  4. stirringstirred for 30 minutes
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-62936ad7cff54f01a89a414a0e641cb5
出典データセット
uspto-grants-2014_09
特許番号
US08822494B2

反応ノート

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