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

HRID 11318

反応式

HRID 11318 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e465fd2a4d7d484db6d6c5f3ee938d03
出典データセット
uspto-grants-2006_08
特許番号
US07098211B2

関連ノート

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