Hydrazine hydrate (1:1) → HCID 178435583、化合物

HRID 1921358ノート

反応式

HRID 1921358 の反応式
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([O:15][CH3:16])=[N:9][C:8]=1[CH3:17])C.O.[NH2:20]N>C(O)(=O)C>[CH2:13]([C:11]1[C:10]([O:15][CH3:16])=[N:9][C:8]([CH3:17])=[C:7]([C:6]2[N:5]=[CH:4][NH:2][N:20]=2)[CH:12]=1)[CH3:14]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 67492560N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide

生成物 1

HCID 178435583HCID 178435583、化合物収率 52%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

In a round bottom flask under a nitrogen atmosphere N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide (synthesized on 0.309 mmol scale) is treated with glacial acetic acid (1 mL) followed by hydrazine hydrate (16.5 μL, 0.340 mmol). The resulting mixture is stirred at 90° C. for 3.75 hr. The reaction mixture is evaporated, then partitioned between water and dichloromethane and the pH adjusted to 6-7 by treating with solid sodium bicarbonate. The aqueous layer is separated and then further extracted with five portions of dichloromethane. The combined extract is dried over magnesium sulfate, filtered and evaporated to give 3-ethyl-2-methoxy-6-methyl-5-(1H-1,2,4-triazol-3-yl)-pyridine (35 mg, 52% yield, 2 steps) as a white solid. MS: m/e=219 (M+H); 1H NMR (300 MHz, CDCl3, δ, ppm): 11.52 (1H, s), 8.18 (1H, s), 7.78 (1H, s), 3.98 (3H, s), 2.68 (3H, s), 2.57 (2H, q), 1.19 (3H, t).

後処理

  1. customThe reaction mixture is evaporated
  2. custompartitioned between water and dichloromethane
  3. additionby treating with solid sodium bicarbonate
  4. customThe aqueous layer is separated
  5. extractionfurther extracted with five portions of dichloromethane
  6. extractionThe combined extract
  7. dry with materialis dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-f8e250c56ef941f2a1021429800e7c13
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

読み込み中…