Phosphorus oxychloride → 1-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

HRID 1850865ノート

反応式

HRID 1850865 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH2:16][CH2:15][N:14]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 604097221-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide

生成物 1

HCID 668686991-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

1-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide (10.58 g, 30.8 mmol) was treated with toluene (100 mL). Phosphoryl trichloride (4.72 g, 30.8 mmol) was added and the reaction mixture was heated under reflux for 8 h. After cooling to room temperature the reaction mixture was concentrated in vacuo and then slowly poured in ice water. Ethyl acetate was added and the organic layer was washed with water (2×), dried (MgSO4) and concentrated in vacuo to give an orange oil. Yield: 10.25 g.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 8 h
  3. concentrationwas concentrated in vacuo
  4. additionslowly poured in ice water
  5. additionEthyl acetate was added
  6. washthe organic layer was washed with water (2×)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil

出典と根拠

ORDレコード
ord-ce8f1dd75fe04c46b1a05344fcb0709a
出典データセット
uspto-grants-2015_02
特許番号
US08957089B2

反応ノート

読み込み中…