Dipropylamine → 2-Chloro-6-methylpyridine-4-carbonitrile

HRID 14231

반응식

HRID 14231 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6].[CH2:11]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH3:13]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6].[CH2:11]([N:14]([CH2:15][CH2:16][CH3:17])[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6])[CH2:12][CH3:13]

참가 물질

4

반응물 2

HCID 8902DipropylamineHCID 210854392-Chloro-6-methylpyridine-4-carbonitrile

생성물 2

HCID 210854392-Chloro-6-methylpyridine-4-carbonitrileHCID 210854592-(Dipropylamino)-6-methylisonicotinonitrile

반응 조건

온도
80 °C

실험 절차

To 2-chloro-6-methylisonicotinonitrile (0.230 g, 1.51 mmol) was added di-n-propylamine (5 mL). The mixture was heated at 80° C. in a sealed, thick-walled glass vessel for 12 h and then at room temperature for 17 h. Excess di-n-propylamine was removed under reduced pressure and the residue was partitioned between dichloromethane and aq. sodium bicarbonate. After drying over sodium sulfate and concentration, the residue was chromatographed on silica gel using ethyl acetate-hexane (10/90) to give 0.14 g of 2-chloro-6-methylisonicotinonitrile and 0.059 g of 2-(dipropylamino)-6-methylisonicotinonitrile. Using the above conditions, 2-chloro-6-methylisonicotinonitrile (0.14 g) was converted to an additional 0.043 g of 2-(dipropylamino)-6-methylisonicotinonitrile.

후처리

  1. customExcess di-n-propylamine was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and aq. sodium bicarbonate
  3. dry with materialAfter drying over sodium sulfate and concentration
  4. customthe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-4846e938218741aeaf262d9689c8572c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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