Nitric Acid → N-[4-(1-Cyanoethyl)-2-nitrophenyl]acetamide

HRID 660353ノート

反応式

HRID 660353 の反応式
[C:1]([CH:3]([CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)#[N:2].CC(OC(C)=O)=O.[N+:22]([O-])([OH:24])=[O:23]>O>[C:1]([CH:3]([CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([N+:22]([O-:24])=[O:23])[CH:5]=1)#[N:2]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12226815N-(4-(1-Cyanoethyl)phenyl)acetamide

生成物 1

HCID 12226816N-[4-(1-Cyanoethyl)-2-nitrophenyl]acetamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To the flask of N-[4-(Cyano-methyl-methyl)-phenyl]-acetamide (12.9 g, 68.5 mmol) was added Ac2O (35 mL) at 5° C. The mixture was stirred and added HNO3 (7.45 g, 70.9 mmol) at 0° C. This reaction was very exothermic. The mixture was stirred for 1 hr at 0° C. and additionally stirred for 3 hrs at room temperature. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant.

後処理

  1. stirringThe mixture was stirred for 1 hr at 0° C.
  2. stirringadditionally stirred for 3 hrs at room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-4939fcbcdbbe45e4bb76fcfa695e497b
出典データセット
uspto-grants-2011_12
特許番号
US08084484B2

反応ノート

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