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

HRID 457313ノート

反応式

HRID 457313 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-26ac92c8985b4770be47cd54627d38e3
出典データセット
uspto-grants-2007_03
特許番号
US07186743B2

反応ノート

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