Ethyl 4-(3-chloropropoxy)benzoate → ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoate

HRID 346231ノート

反応式

HRID 346231 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14]Cl)=[CH:7][CH:6]=1)[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:7][CH:6]=1)[CH3:2]

参加物

4

反応物 2

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoateHCID 24194345Phthalimide potassium salt

生成物 1

HCID 52199766ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoate収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

To a stirred solution of 22.5 g (0.092 mole) of 4-(3-chloropropoxy)benzoic acid ethyl ester in 150 mL of dimethylformamide was added 17.6 g (0.093 mole) of potassium phthalimide (98%, Aldrich) and the mixture was heated (135° C.) under a nitrogen atmosphere for 8 hr. The solvent was evaporated under reduced pressure to leave a semi-solid residue. The residue was triturated with 100 mL of water and the resulting solid was collected by filtration. The solid was recrystallized from isopropyl alcohol to yield 18.2 g (55%) of title compound as an off-white solid, mp 106°-108° C.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customto leave a semi-solid residue
  3. customThe residue was triturated with 100 mL of water
  4. filtrationthe resulting solid was collected by filtration
  5. customThe solid was recrystallized from isopropyl alcohol

出典と根拠

ORDレコード
ord-5b2a426afd5b47d6ac3fd459e8cc4820
出典データセット
uspto-grants-1991_10
特許番号
US05061720

反応ノート

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