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

HRID 2356636

反応式

HRID 2356636 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d24b44417134b4da603490b1d99dbfc
出典データセット
uspto-grants-2010_07
特許番号
US07759369B2

関連ノート

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