4-Bromoanisole → 6-[4-methoxyphenyl]-2-(1H)-quinolone

HRID 568345ノート

反応式

HRID 568345 の反応式
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.I[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]2>CCCCC.O1CCCC1.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]3)=[CH:8][CH:9]=1

参加物

8

反応物 3

HCID 77304-BromoanisoleHCID 138361846-Iodoquinolin-2(1H)-oneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 201504516-[4-methoxyphenyl]-2-(1H)-quinolone

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of t-butyl lithium (9.0 cm3 of a 2.0M solution in n-pentane) was added at -70° to a stirred solution of 4-bromoanisole (1.13 cm3) in tetrahydrofuran (THF) (20 cm3) under nitrogen. After 10 minutes a solution of anhydrous zinc chloride (1.23 g) in THF (10 cm3) was added and the mixture was allowed to warm to room temperature over 0.5 hour. A mixture of 6-iodo-2-(1H)-quinolone (0.813 g) and tetrakis(triphenylphosphine) palladium (0) (0.03 g) was added and the mixture was heated under reflux for 2 hours. Volatile material was then removed in vacuo and the residue was partitioned between chloroform:methanol, 9:1 (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (7 g) in water (100 cm3). The aqueous phase was further extracted with chloroform:methanol, 9:1 (3×100 cm3), and the combined and dried (MgSO4) organic extracts were evaporated to give an oily solid which was triturated with ethyl acetate. Recrystallization of the residue from ethyl acetate-methanol-chloroform afforded the title compound, m.p. 262°-264° (0.359 g).

後処理

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customVolatile material was then removed in vacuo
  5. customthe residue was partitioned between chloroform
  6. extractionThe aqueous phase was further extracted with chloroform
  7. dry with materialdried (MgSO4) organic extracts
  8. customwere evaporated
  9. customto give an oily solid which
  10. customwas triturated with ethyl acetate
  11. customRecrystallization of the residue from ethyl acetate-methanol-chloroform

出典と根拠

ORDレコード
ord-d435d54016c24574b809300198fda8e7
出典データセット
uspto-grants-1988_03
特許番号
US04728654

反応ノート

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