Dimethylformamide → 6-phenoxy-1H-indole

HRID 1371963ノート

反応式

HRID 1371963 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]N(C=O)C>>[O:1]([C:8]1[CH:9]=[C:10]2[C:11]([CH:14]=[CH:18][NH:15]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 6228DimethylformamideHCID 210715624-Phenoxy-1-methyl-2-nitrobenzene

生成物 1

HCID 210716106-phenoxy-1H-indole

実験手順

Combine 4-phenoxy-1-methyl-2-nitro-benzene (6 g, 26.2 mmol) and DMF dimethylacetal (15.6 g, 131 mmol) in 60 mL dry DMF and heat at 170° C. for 16 hours. Cool to room temperature and concentrate to dryness. Dissolve residue in 50 mL EtOAc and hydrogenate with 2 g 5% Pd/C and hydrogen for 3 hours at atmospheric pressure. Filter through celite and concentragte to an oil. Purify by chromatography using Hex/EtoAC to obtain a tan solid: ISMS 210 (M+1) 1H NMR (CDCl3) 8.08 (bs, 1H), 7.61–7.59 (m, 1H), 7.34–7.29 (m, 2H), 7.18–7.17 (m, 1H), 7.18–7.0 (m, 4H), 6.92–6.89 (m, 1H), 6.56–6.54 (m, 1H).

後処理

  1. concentrationconcentrate to dryness
  2. filtrationFilter through celite and concentragte to an oil
  3. customPurify by chromatography
  4. customto obtain a tan solid

出典と根拠

ORDレコード
ord-2705b355770f45219c177426895becf6
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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