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

HRID 1371890

Reaction equation

HRID 1371890 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 112412535-phenoxy-1H-indole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-106d28dc5c944e1bad71daa18b56160f
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Linked notes

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