Hydrazine hydrate (1:1) → Methyl 4-(1H-pyrazol-5-yl)benzoate

HRID 59867

반응식

HRID 59867 반응식
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=O.O.[NH2:19]N>CCO>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)=[N:19]1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)2회HCID 10561611Methyl 4-[3-(dimethylamino)prop-2-enoyl]benzoate

생성물 1

HCID 178497540Methyl 4-(1H-pyrazol-5-yl)benzoate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

To a solution of crude (E)-methyl 4-(3-(dimethylamino)acryloyl)benzoate (28.1 mmol) in EtOH (100 mL) was added hydrazine monohydrate (1.50 mL, 30.9 mmol) and the reaction was heated at 50° C. for 24 hours. The reaction temperature was then increased to 60° C. for 24 hours. Additional hydrazine monohydrate (1.5 mL) was added, and the reaction was heated at 60° C. for an additional 6 hours. The reaction was cooled, concentrated, and dried in a vacuum oven at 45° C. overnight to yield methyl 4-(1H-pyrazol-3-yl)benzoate as an orange solid (8.15 g, quantitative): mp 106° C. (dec); 1H NMR (400 MHz, CDCl3) δ 8.15-8.05 (m, 2H), 7.91-7.83 (m, 2H), 7.65 (d, J=2.4 Hz, 1H), 6.71 (d, J=2.3 Hz, 1H), 3.94 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 166.91, 136.89, 131.83, 130.13, 129.37, 125.50, 103.35, 52.14, 22.46; EIMS m/z 202.

후처리

  1. temperatureThe reaction temperature was then increased to 60° C. for 24 hours
  2. temperaturethe reaction was heated at 60° C. for an additional 6 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customdried in a vacuum oven at 45° C. overnight

출처 및 근거

ORD 기록
ord-108ce89eedd14067ada32e2e5931bf58
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440964B2

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