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

HRID 968109노트

반응식

HRID 968109 반응식
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

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178429282HCID 178429282, 화합물

생성물 1

HCID 222917476-Chloro-4-methylpyridine-3-carboxylic acid수율 81%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7eb2b1e3d384d57a246edba14086373
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956052B2

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