Carbon Dioxide → 2,6-Dichloro-4-methoxynicotinic Acid

HRID 1753892노트

반응식

HRID 1753892 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.C([Li])CCC.[C:16](=[O:18])=[O:17].Cl>C1COCC1>[Cl:1][C:2]1[C:7]([C:16]([OH:18])=[O:17])=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[N:3]=1

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 33199932,6-Dichloro-4-methoxypyridineHCID 178418339Butyllithium

생성물 1

HCID 593100972,6-Dichloro-4-methoxynicotinic Acid수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4.0 g (22.5 mmol) 2,6-dichloro-4-methoxy-pyridine in THF (20 ml) was added 10.0 ml (2.47 M in hexane, 24.7 mmol) n-butyllithium at −78° C. After stirring for 1 h at −78° C. excess dry ice was added and the mixture was allowed to warm to RT. Then the mixture was acidified with 6N aqueous hydrochlorid acid to pH 3-4 followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 3.5 g (15.8 mmol, 70%) 2,6-dichloro-4-methoxy-pyridine-3-carboxylic acid.

후처리

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-b5cb3af8d0bc471aa893c4a3d9339619
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09168259B2

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