Phosphorus oxychloride → 6-Chloro-4-methylpyridine-3-carboxylic acid

HRID 968109ノート

反応式

HRID 968109 の反応式
O[C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>O>[CH3:11][C:9]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=[C:2]([Cl:14])[CH:10]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178429282HCID 178429282、化合物

生成物 1

HCID 222917476-Chloro-4-methylpyridine-3-carboxylic acid収率 81%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

6-Hydroxy-4-methylnicotinic acid (10 g, 65.3 mmol) and phosphorus oxychloride (33 mL) were combined and refluxed for 3 hours. The reaction solution was poured into 300 mL of ice and then 600 mL of water was added. The solution was boiled for 30 minutes before cooling and extracting the product into ether. The solvent was removed and the residue was recrystallized from 900 mL of hot water. Yellow solid, 9.06 g (81% yield). Mp 170-172° C. 1H NMR (CD3OD): δ 2.61 (s, 3H), 7.41 (s, 1H), 8.80 (s, 1H). LC-MS, M+1=172.

後処理

  1. temperaturerefluxed for 3 hours
  2. temperaturebefore cooling
  3. extractionextracting the product into ether
  4. customThe solvent was removed
  5. customthe residue was recrystallized from 900 mL of hot water

出典と根拠

ORDレコード
ord-c7eb2b1e3d384d57a246edba14086373
出典データセット
uspto-grants-2005_10
特許番号
US06956052B2

反応ノート

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