Methanol → Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

HRID 323554ノート

反応式

HRID 323554 の反応式
O.[ClH:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([OH:11])=[O:10].[CH3:12]O>S(Cl)(Cl)=O>[ClH:2].[Cl:2][C:6]1[CH:7]=[CH:8][N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1

参加物

5

反応物 3

HCID 887MethanolHCID 962WaterHCID 715592-Pyridinecarboxylic acid, hydrochloride (1:1)

生成物 1

HCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)収率 85%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

H2O (18 mL) was added dropwise to a stirred suspension of picolinic acid hydrochloride, compound 1 (157.9 g, 1.0 mol) in thionyl chloride (400 mL). The resulting mixture was heated under reflux for 4 days giving a clear orange solution. After cooling to ambient temperature, the solution was concentrated to a syrup and the residue coevaporated with toluene (2×500 mL). The residue was dissolved in toluene (1 L) and cooled to 0-5° C. Methanol (44.0 g, 1.0 mol) was added dropwise to the ice cold reaction mixture giving a heavy white precipitate. This precipitate was collected by filtration, washed with toluene (3×100 mL) and dried at 40° C. for 24 hr to give 176.5 g (85%) of compound 2 as a white crystalline solid.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 4 days
  3. customgiving a clear orange solution
  4. concentrationthe solution was concentrated to a syrup
  5. dissolutionThe residue was dissolved in toluene (1 L)
  6. temperaturecooled to 0-5° C
  7. customgiving a heavy white precipitate
  8. filtrationThis precipitate was collected by filtration
  9. washwashed with toluene (3×100 mL)
  10. customdried at 40° C. for 24 hr

出典と根拠

ORDレコード
ord-970a2631170a436496ee49664a2bb69b
出典データセット
uspto-grants-2001_04
特許番号
US06214801B1

反応ノート

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