N-[4-(hydroxymethyl)-3-methylphenyl]acetamide → N-(4-Formyl-3-methylphenyl)acetamide

HRID 534760노트

반응식

HRID 534760 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13])=[O:1]

참가 물질

4

반응물 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

생성물 1

HCID 12931765N-(4-Formyl-3-methylphenyl)acetamide수율 92%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

N-[4-(Hydroxymethyl)-3-methylphenyl]acetamide (D77) (0.36 g, 2 mmol) and manganese dioxide (0.875 g, 10 mmol) were combined in acetonitrile (16 mL) and heated to 120° C. in the microwave for 7 minutes. The MnO2 was filtered off and the reaction mixture was concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.17 (1H, s), 7.77 (1H, d), 7.51 (1H, d), 7.45 (1H, s), 7.36 (1H, br.s), 2.66 (3H, s), 2.22 (3H, s). MS (ES): MH+ 178.2.

후처리

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. customto give the crude product which
  4. customwas purified by column chromatography
  5. washElution with 0-100% ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-f6dd7cd0e5a146878c250bf331eefd96
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853218B2

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