Benzene → HCID 18379655, compound

HRID 2299032Notes

Reaction equation

HRID 2299032 reaction equation
CCCCCON=O.[Br:9][C:10]1[CH:16]=[CH:15][C:13](N)=[C:12]([O:17][CH3:18])[CH:11]=1.[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[Br:9][C:10]1[CH:16]=[CH:15][C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([O:17][CH3:18])[CH:11]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 10026Pentyl nitriteHCID 4592574-Bromo-2-methoxyaniline

Product 1

HCID 18379655HCID 18379655, compound

Procedure

n-Amyl nitrite (8.1 ml, 60 mmol) was slowly added to a stirred mixture of 4-bromo-2-methoxyaniline (J.Med.Chem., 1989, 32, 1936; 8.1 g, 60 mmol) and benzene (175 ml), under nitrogen, at about 50° C. When the addition was complete, the reaction mixture was heated under reflux for about 3 hours, then allowed to cool to room temperature and evaporated under reduced pressure. The residue was azeotroped with tetrahydrofuran, then with ethyl acetate, and purified by flash chromatography, using an elution gradient of hexane:ethyl acetate (100:0 to 95:5) to give the title compound (1.66 g) as a colourless solid, m.p. 50-52° C. δ(CDCl3): 3.77 (s,3H), 7.08 (s,1H), 7.14 (s,2H), 7.30 (m,1H), 7.36-7.41 (m,2H), 7.41-7.49 (m,2H).

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for about 3 hours
  4. customevaporated under reduced pressure
  5. customThe residue was azeotroped with tetrahydrofuran
  6. customwith ethyl acetate, and purified by flash chromatography

Sources & evidence

ORD record
ord-e485658fde7c4697aef30940318f4b15
Source dataset
uspto-grants-2002_12
Patent number
US06495568B1

Reaction notes

Loading…