Dimethylformamide → 6-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acid

HRID 2356636

반응식

HRID 2356636 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]CC2C=CC(Cl)=CC=2F)=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.C[S-].[Na+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 59384237Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

생성물 1

HCID 684564716-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acid수율 76%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}-phenyl)methyl]-2-pyridinecarboxylate (453 mg), sodium thiomethoxide (370 mg) and dimethylformamide (5 ml) was stirred at 100° C. for 2.5 hours. After cooling water (30 ml) was added and the mixture extracted with ethyl acetate (2×25 ml). The aqueous layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (10 ml), dried (MgSO4) and concentrated in vacuo. The residue was washed with water and recrystallised from ether to afford the title compound (208 mg, 76%) as a pale buff solid.

후처리

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (2×25 ml)
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. washThe combined extracts were washed with water (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with water
  8. customrecrystallised from ether

출처 및 근거

ORD 기록
ord-4d24b44417134b4da603490b1d99dbfc
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759369B2

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