Nitric Acid → 2-Chloro-6-methyl-5-nitrobenzonitrile

HRID 52633

반응식

HRID 52633 반응식
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[C:8]#[N:9]>>[Cl:5][C:6]1[CH:13]=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[C:10]([CH3:14])[C:7]=1[C:8]#[N:9]

참가 물질

3

반응물 2

HCID 944Nitric AcidHCID 230532-Chloro-6-methylbenzonitrile

생성물 1

HCID 129530402-Chloro-6-methyl-5-nitrobenzonitrile

실험 절차

Under a nitrogen atmosphere, a stirred solution of aqueous 90% nitric acid was cooled to -35° C., and 40.0 grams (0.264 mole) of 2-chloro-6-methylbenzonitrile was added in one portion. The reaction mixture was then allowed to warm to ambient temperature, where it was stirred for about 18 hours. After this time, the reaction mixture was poured into 3000 mL of ice-water. After the ice melted, the resultant solid was collected by filtration and dried. The NMR spectrum of the solid indicated that it was about 75% pure product. The solid was recrystallized twice from methanol, yielding 13.9 grams of 2-chloro-6-methyl-5-nitrobenzonitrile, mp 85.5°-87.5° C. The NMR spectrum was consistent with the proposed structure. The filtrates from the recrystallizations were combined and concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10% ethyl acetate in petroleum ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding an additional 20.4 grams of 2-chloro-6-methyl-5-nitrobenzonitrile, mp 87.5°-89.5° C. The NMR spectrum was consistent with the proposed structure.

후처리

  1. filtrationthe resultant solid was collected by filtration
  2. customdried
  3. customThe solid was recrystallized twice from methanol

출처 및 근거

ORD 기록
ord-0e14d4aef85443348a32ca44e54e2dff
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616718

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