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

HRID 728770

反応式

HRID 728770 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 3453642-Chloro-4-methyl-5-nitropyridine収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b16f6c0d450342a2ba5c77bfdc929048
出典データセット
uspto-grants-1991_09
特許番号
US05051412

関連ノート

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