Hydrazine hydrate (1:1) → HCID 178435583, 화합물

HRID 1921358노트

반응식

HRID 1921358 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178435583HCID 178435583, 화합물수율 52%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8e250c56ef941f2a1021429800e7c13
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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