Trifluoroacetic anhydride → 2,6-dichloro-4-methyl-nicotinic acid-N-oxide

HRID 1711151ノート

反応式

HRID 1711151 の反応式
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].C(N)(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N+:10]([O-:14])=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5]

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

生成物 1

HCID 866295192,6-dichloro-4-methyl-nicotinic acid-N-oxide収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,6-Dichloro-4-methyl-nicotinic acid (0.234 g, 1.14 mmol) and hydrogen peroxide-urea adduct (0.537 g, 5.70 mmol) were suspended in CH2Cl2 to give a white slurry. Trifluoroacetic anhydride (0.65 ml, 4.67 mmol) was added dropwise over 5 minutes and the resulting pale yellow solution was stirred overnight at rt. The reaction mixture was quenched with water (10 ml) and then dry loaded onto silica gel and purified using column chromatography (MeCN/MeOH/NH4OH, 8:1:1, v/v/v) to give 2,6-dichloro-4-methyl-nicotinic acid-N-oxide as a pale yellow crystalline solid (0.103 g, 41%). 1H NMR (CD3OD) δ 2.37 (s, 3H), 7.60 (s, 1H).

後処理

  1. customto give a white slurry
  2. customThe reaction mixture was quenched with water (10 ml)
  3. customdry
  4. custompurified

出典と根拠

ORDレコード
ord-b5406a60f8f04922b3fbc74c06b42ece
出典データセット
uspto-grants-2010_09
特許番号
US07790747B2

反応ノート

読み込み中…