Dimethylformamide → 6-phenoxy-1H-indole

HRID 1371963Notes

Reaction equation

HRID 1371963 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 210716106-phenoxy-1H-indole

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2705b355770f45219c177426895becf6
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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