Nitric Acid → 1-(4-Methylphenyl)-4-nitropyrrole-2-carbonitrile

HRID 248365노트

반응식

HRID 248365 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrile

생성물 1

HCID 197594701-(4-Methylphenyl)-4-nitropyrrole-2-carbonitrile

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

To a solution of 1-(4-methylphenyl)pyrrole-2-carbonitrile (1.0 g) in acetic anhydride (4 ml) was added nitric acid (231 μl, 94%) dropwise at 5° C. The mixture was stirred at the same temperature for 3 hours and then poured into ice water. The pH was adjusted to 5-7 by the addition of saturated aqueous sodium bicarbonate solution. The separated oil was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography to yield 1-(4-methylphenyl)-4-nitropyrrole-2-carbonitrile (471 mg) as a solid.

후처리

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-69ff63ce454d4085878896b9e6894c5d
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210092

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