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

HRID 730897노트

반응식

HRID 730897 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 2782166Methyl 5,6-Dichloronicotinate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1a7209e737be4e12984521e26c14e45b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582761B2

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