Thionyl Chloride → 2-Chloro-4-methyl-5-nitropyridine

HRID 728770

반응식

HRID 728770 반응식
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][NH:5][C:4](=O)[CH:3]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 3453714-Methyl-5-nitro-1,2-dihydropyridin-2-one

생성물 1

HCID 3453642-Chloro-4-methyl-5-nitropyridine수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours. The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride. The residual oil then passed througha silica gel filter (dried at 150° C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1). This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95%) as an orange oil, which crystallized below 0° C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1 ; 1H NMR (CDCl3) δ 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36).

후처리

  1. temperaturewas heated atreflux under nitrogen for 52 hours
  2. customThe resultant orange colored solution was evaporated under reduced pressure
  3. additiona small amount of anhydrous toluene was added
  4. customremoved via evaporation under reduced pressure
  5. customto remove traces of thionyl chloride
  6. filtrationfilter
  7. custom(dried at 150° C. under vacuum overnight, approximately 100 g)
  8. customThis filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b16f6c0d450342a2ba5c77bfdc929048
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051412

연결된 노트

불러오는 중…