Dimethylformamide → 6-phenoxy-1H-indole

HRID 1666891Notes

Reaction equation

HRID 1666891 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 concentrate to an oil. Purify by chromatography using Hex/EtoAC to obtain a tan solid: ISMS 210 (M+1)

Workup

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

Sources & evidence

ORD record
ord-c329c613c222484482a8224f44d64b02
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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