Thionyl Chloride → HCID 20464099, compound

HRID 1434555Notes

Reaction equation

HRID 1434555 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([OH:14])=O)([O-:3])=[O:2].S(Cl)([Cl:17])=O>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([Cl:17])=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 748183-(2-Nitrophenyl)propionic acid

Product 1

HCID 20464099HCID 20464099, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-nitrophenyl)propanoic acid (1.20 g, 6.15 mmol) and thionyl chloride (0 878 g, 7.38 mmol) in dichloromethane (5 ml) was stirred and heated to reflux for 2 hours. The mixture was concentrated under reduced pressure to obtain 3-(2-nitrophenyl)propanoyl chloride. To the obtained crude 3-(2-nitrophenyl)propanoyl chloride (1.31 g, 6.15 mmol) was added CS2, and aluminum trichloride (1.07 g, 8.0 mmol) was added portionwise at 0° C. The mixture was stirred at 70° C. for 3 hours, and after cooled to ambient temperature, water was added and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethylacetate 10:1) to afford 4-nitroindan-1-one (0.44 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc4590bbd9df4ea89f35612cb9069756
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

Loading…