Lithium Chloride → 4-Chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile

HRID 506157

반응식

HRID 506157 반응식
COC1C=C(C=CC=1OC)C[N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:14]=2)[C:10](=O)[C:9]([C:27]#[N:28])=[CH:8]1.[Cl-:34].[Li+]>O=P(Cl)(Cl)Cl>[Cl:34][C:10]1[C:9]([C:27]#[N:28])=[CH:8][N:7]=[CH:12][C:11]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:14]=1

참가 물질

4

반응물 2

HCID 433294Lithium ChlorideHCID 68466370HCID 68466370, 화합물

생성물 1

HCID 684653034-Chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile수율 78.2%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

A solution of 1-(3,4-dimethoxybenzyl)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-oxo-1,4-dihydro-pyridine-3-carbonitrile (300 mg, 0.666 mmol) and lithium chloride (LiCl, 254 mg, 6 mmol) in 2.5 mL of POCl3 was heated at reflux for 2.5 h. The excess POCl3 was removed by evaporating in vacuo and then was co-evaporated with toluene. The residue was dissolved in 100 mL ethyl acetate and washed with ice-cold 1 N aqueous sodium hydroxide. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated in vacuo, and the resulting solid was triturated with isopropyl alcohol to yield 166 mg (78% yield) of 4-chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-nicotinonitrile as an off-white solid.

후처리

  1. temperatureat reflux for 2.5 h
  2. customThe excess POCl3 was removed
  3. customby evaporating in vacuo
  4. dissolutionThe residue was dissolved in 100 mL ethyl acetate
  5. washwashed with ice-cold 1 N aqueous sodium hydroxide
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe resulting solid was triturated with isopropyl alcohol

출처 및 근거

ORD 기록
ord-ab54470b12b343b68d52b0f62a9f8211
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781591B2

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