Nitric Acid → N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide

HRID 634739

反応式

HRID 634739 の反応式
[Sn](Cl)(Cl)(Cl)Cl.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([CH3:22])[CH:13]=1>C(Cl)Cl>[CH3:10][O:11][C:12]1[C:17]([N+:6]([O-:9])=[O:7])=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([CH3:22])[CH:13]=1

参加物

5

反応物 3

HCID 944Nitric AcidHCID 24287Tin tetrachlorideHCID 95082N-(4-Methoxy-2-methylphenyl)-acetamide

生成物 1

HCID 21260362N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-30 °C

実験手順

A mixture of tin(IV)chloride (1 9.3 ml) and 69.5% nitric acid (10.3 ml) in methylene chloride (140 ml) was added dropwise to a solution of N-(4-methoxy-2-methylphenyl)acetamide (28 g, 0.14 mol) in methylene chloride (500 ml) cooled to and maintained at −30° C. The reaction mixture was stirred at −30° C. for 1.5 hours, allowed to warm to ambient temperature then poured on to ice/water. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined extracts were dried (MgSO4), the solvent removed by evaporation and the residue purified by column chromatography eluting with petroleum ether/ethyl acetate (2/8) to give N-(4-methoxy-2-methyl-5-nitrophenyl)acetamide (1 7.8 g, 51%)

後処理

  1. temperaturecooled to and
  2. temperatureto warm to ambient temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customthe residue purified by column chromatography
  8. washeluting with petroleum ether/ethyl acetate (2/8)

出典と根拠

ORDレコード
ord-011c050cf513429c849dbcb76c2debdc
出典データセット
uspto-grants-2001_02
特許番号
US06184225B2

関連ノート

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