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

HRID 568345Notes

Reaction equation

HRID 568345 reaction equation
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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d435d54016c24574b809300198fda8e7
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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