Dimethylformamide → 5-Butyl-2-chloro-nicotinic acid methyl ester

HRID 2100551노트

반응식

HRID 2100551 반응식
O(Cl)[Cl:2].[CH3:4][O:5][C:6](=[O:16])/[C:7](/C#N)=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[N:18]([CH:20]=O)[CH3:19]>>[CH3:4][O:5][C:6](=[O:16])[C:7]1[CH:8]=[C:9]([CH2:10][CH2:11][CH2:12][CH3:13])[CH:20]=[N:18][C:19]=1[Cl:2]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24646Chlorine monoxideHCID 86616607(E)-2-cyano-oct-2-enoic acid methyl ester

생성물 1

HCID 866166085-Butyl-2-chloro-nicotinic acid methyl ester수율 17%

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온도
80 °C

실험 절차

Phosporous oxychloride (4.76 ml, 51 mmol) was added within 10 minutes to an ice cold solution of (E)-2-cyano-oct-2-enoic acid methyl ester (4.65 g, 26 mmol) in DMF (12 ml) under an argon atmosphere. The reaction mixture was stirred for 14 h at 80° C. and poured onto ice water. After 3 h the mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water and dried over sodium sulfate. Removal of the solvent under reduced pressure left a brown oil which was purified by column chromatography (silica gel, isopropyl acetate/heptane) to give 5-butyl-2-chloro-nicotinic acid methyl ester (1.01 g, 4.4 mmol; 17%) as yellow oil. MS: m/e=227.0 [M+H+].

후처리

  1. additionpoured onto ice water
  2. extractionAfter 3 h the mixture was extracted two times with dichloromethane
  3. washthe combined extracts were washed with ice water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. waitleft a brown oil which
  7. customwas purified by column chromatography (silica gel, isopropyl acetate/heptane)

출처 및 근거

ORD 기록
ord-a067bf2053a04d929045bebf64a1c771
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572801B2

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