Dimethylformamide → Methyl 2-chloro-6-methylpyridine-3-carboxylate

HRID 423239

반응식

HRID 423239 반응식
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]N(C)C=O.CN(C1C=CC=CN=1)C.C(N=C=NCCCN(C)C)C>CO.C(Cl)(Cl)Cl>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:2]=1[Cl:1]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 1217242-Chloro-6-methylnicotinic acid

생성물 1

HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

2-Chloro-6-methylnicotinic acid (25.0 g) was suspended in a mixed solvent of dimethylformamide (100 mL) and chloroform (100 mL), and to this suspension were added dimethylaminopyridine (21.3 g) and methanol (4.67 g). Finally, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (WSC) hydrochloride (33.5 g) was added to the mixture, followed by stirring at room temperature for 6 hours. After the reaction mixture was concentrated, ethyl acetate (300 mL) was added thereto. The mixture was washed successively with water, 10% ammonium chloride, water, and saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4, v/v) to give the title compound (24.6 g) as a colorless oil.

후처리

  1. concentrationAfter the reaction mixture was concentrated
  2. additionethyl acetate (300 mL) was added
  3. washThe mixture was washed successively with water, 10% ammonium chloride, water, and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4, v/v)

출처 및 근거

ORD 기록
ord-a1d58fef6697485a90289a87032fa20f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101774B2

연결된 노트

불러오는 중…