5,6-Dichloronicotinic acid → Methyl 5,6-Dichloronicotinate

HRID 730897

反応式

HRID 730897 の反応式
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[C:3]([Cl:11])=[N:4][CH:5]=1

参加物

4

反応物 2

HCID 2479875,6-Dichloronicotinic acidHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 2782166Methyl 5,6-Dichloronicotinate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 5,6-dichloro-nicotinic acid (1.92 g, 10 mmol, Aldrich) and p-toluenesulfonic acid monohydrate (190 mg, 1.0 mmol, Aldrich) in methanol (5 mL, Aldrich) was heated at reflux for 25 h. The reaction mixture was cooled to room temperature, the solvent was removed in vacuo and the residue was dissolved in EtOAc (50 mL). The solution was washed with satd. NaHCO3 (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 30% EtOAc/hexane to give the title compound as a white solid. MS ESI, pos. ion) m/e: 205 (M+1).

後処理

  1. temperatureat reflux for 25 h
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washThe solution was washed with satd
  5. dry with materialNaHCO3 (20 mL) and brine (20 mL), dried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with 30% EtOAc/hexane

出典と根拠

ORDレコード
ord-1a7209e737be4e12984521e26c14e45b
出典データセット
uspto-grants-2009_09
特許番号
US07582761B2

関連ノート

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