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

HRID 660353노트

반응식

HRID 660353 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4939fcbcdbbe45e4bb76fcfa695e497b
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084484B2

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