Potassium Carbonate → 6-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 1590789ノート

反応式

HRID 1590789 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[C:26]([CH2:25][CH2:24][CH2:23][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:3][C:2]=1[Cl:1])([O:28][CH2:29][CH3:30])=[O:27]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1355888616-(3-chloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

生成物 1

HCID 136876936-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone収率 75.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 1.500 mg (6.675 mmol) of 6-(3-chloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone, prepared by the method of Eur. Pat. Appl. 178,189, 1.010 g (7.34 mmol) K2CO3, and 1.463 g (7.50 mmol) of ethyl 4-bromobutyrate in 30 ml of DMF is heated at 100° C. for 2 hrs under N2. The DMF is removed under vacuum and the residue taken up in 150 ml of EtOAc and 50 ml of water. The organic phase is washed with 50 ml of 5% NaOH, then saturated NaCl solution, dried (MgSO4), and the solvent removed to leave a white solid. This solid is recrystallized from hexane-EtoAc to give 1.711 g of 6-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone as white needles, m.p. 109°-110° C. Yield, 82%.

後処理

  1. customprepared by the method of Eur
  2. customThe DMF is removed under vacuum
  3. washThe organic phase is washed with 50 ml of 5% NaOH
  4. dry with materialsaturated NaCl solution, dried (MgSO4)
  5. customthe solvent removed
  6. customto leave a white solid
  7. customThis solid is recrystallized from hexane-EtoAc

出典と根拠

ORDレコード
ord-81809baae0bc439e8b9aa391b6eda72b
出典データセット
uspto-grants-1993_04
特許番号
US05204463

反応ノート

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