2-Chloronicotinic acid → 2-(2-Methylpropoxy)pyridine-3-carboxylic acid

HRID 354161노트

반응식

HRID 354161 반응식
[Na].Cl[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>C(O)C(C)C>[CH2:5]([O:6][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH:4]([CH3:8])[CH3:3]

참가 물질

4

반응물 2

HCID 762582-Chloronicotinic acidHCID 5360545Sodium

생성물 1

HCID 235115682-(2-Methylpropoxy)pyridine-3-carboxylic acid수율 168.1%

시약·촉매·용매 1

HCID 6560Isobutanol용매2회

반응 조건

온도
80 °C

실험 절차

Sodium metal (3 g, 0.127 mol) was added in small amounts to isobutanol (100 mL)—some warming (80° C.) was needed to facilitate dissolution. 2-Chloronicotinic acid (10 g, 0.064 mol) was added and the solution refluxed for 1 h. A thick mixture resulted and a further 100 mL isobutanol was added and the mixture refluxed for 3 h. The mixture was cooled and quenched with 2N hydrochloric acid. The product was extracted into ethyl acetate and the organics washed with dilute hydrochloric acid (pH 3), dried (MgSO4) and concentrated to give a brown solid. Purification by flash column chromatography (ethyl acetate as eluant) gave 10.5 g of product as a yellow solid.

후처리

  1. dissolutiondissolution
  2. temperaturethe solution refluxed for 1 h
  3. customA thick mixture resulted
  4. temperaturethe mixture refluxed for 3 h
  5. temperatureThe mixture was cooled
  6. customquenched with 2N hydrochloric acid
  7. extractionThe product was extracted into ethyl acetate
  8. washthe organics washed with dilute hydrochloric acid (pH 3)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a brown solid
  12. customPurification by flash column chromatography (ethyl acetate as eluant)

출처 및 근거

ORD 기록
ord-017b6a9dc9654a8cb6db2f40c208bcf4
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756373B1

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