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

HRID 568345노트

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HRID 568345 반응식
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

참가 물질

8

반응물 3

HCID 77304-BromoanisoleHCID 138361846-Iodoquinolin-2(1H)-oneHCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d435d54016c24574b809300198fda8e7
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04728654

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