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

HRID 534760ノート

反応式

HRID 534760 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6dd7cd0e5a146878c250bf331eefd96
出典データセット
uspto-grants-2014_10
特許番号
US08853218B2

反応ノート

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