N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-phenoxy-1H-indole

HRID 1371890

反応式

HRID 1371890 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:17])([O-])=O.[CH3:18]N(C(N(C)C)N(C)C)C.[H][H]>C1(C)C=CC=CC=1.CCOC(C)=O.[Pd]>[O:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[NH:1][CH:18]=[CH:17]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 27284182-Nitro-5-phenoxytolueneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 112412535-phenoxy-1H-indole

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Combine 2-nitro-5-phenoxytoluene (1.15 g, 5.0 mmol) and tris(dimethylamino)methane (0.87 g, 6.0 mmol) in 10 mL dry toluene and heat to reflux under nitrogen. After 2 hours, cool the reaction mixture to room temperature and evaporate the toluene under reduced pressure to form a residue. Dissolve the residue in 15 mL EtOAc, mix with Pd/C (10%, 100 mg), stir at room temperature under 1 atmosphere of hydrogen for 1.5 days. Filter off catalyst and concentrate the filtrate. Chromatograph on silica gel eluting with hexanes/EtOAc give the title compound as a solid: 1H NMR (300 MHz, CDCl3) 6.49–6.50 (m, 1H), 6.93–7.03 (m, 4H), 7.22–7.27 (m, 5H), 8.15 (br, 1H).

後処理

  1. temperatureto reflux under nitrogen
  2. customevaporate the toluene under reduced pressure
  3. customto form a residue
  4. filtrationFilter off catalyst
  5. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-106d28dc5c944e1bad71daa18b56160f
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

関連ノート

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