Ethyl Acetate → 6-[3-Chloro-4-(ethoxycarbonylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 11318

반응식

HRID 11318 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=O)[CH2:16][CH2:17][C:18]([OH:20])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].O.[NH2:23][NH2:24].C(OCC)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:16][CH2:17][C:18](=[O:20])[NH:23][N:24]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 148782884-[3-Chloro-4-(ethoxycarbonylmethoxy)phenyl]-4-oxobutyric acid

생성물 1

HCID 136876706-[3-Chloro-4-(ethoxycarbonylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone수율 82%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a stirred suspension of 4-[3-chloro-4-(ethoxycarbonylmethoxy)phenyl]-4-oxobutyric acid (9, 21.5 g, 69.2 mmol) in ethanol (200 mL) at 0° C. was added a solution of hydrazine monohydrate (3.4 mL, 69.2 mmol) in ethanol (20 mL). The reaction mixture was then allowed to warm to ambient temperature and stirred at this temperature for 15 minutes before being heated to reflux and stirred at this temperature for 3 hours. Ethyl acetate (40 mL) was added to the hot solution and the mixture was allowed to cool to ambient temperature. The precipitate which formed was filtered off and washed with water (2×100 mL) and cold ethanol (2×100 mL), then dried with suction, then under high vacuum to give 10 as light yellow powder (17.6 g, 82% yield, 99% pure by LCMS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.52 (m, 1H); 7.41 (m, 1H); 6.70 (m, 1H); 4.90 (s, 2H); 4.12 (q, 2H); 2.22 (m, 2H); 1.62 (m, 2H); 1.30 (q, 3H).

후처리

  1. temperaturebefore being heated
  2. temperatureto reflux
  3. stirringstirred at this temperature for 3 hours
  4. temperatureto cool to ambient temperature
  5. customThe precipitate which formed
  6. filtrationwas filtered off
  7. washwashed with water (2×100 mL) and cold ethanol (2×100 mL)
  8. customdried with suction

출처 및 근거

ORD 기록
ord-e465fd2a4d7d484db6d6c5f3ee938d03
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098211B2

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