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

HRID 1666830

반응식

HRID 1666830 반응식
[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

참가 물질

7

반응물 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 27284182-Nitro-5-phenoxytolueneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 112412535-phenoxy-1H-indole

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d46624ab3a94a90b81c09c30a933f9f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044090B2

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