Thionyl Chloride → Methyl 4-chlorocinnoline-3-carboxylate

HRID 1875466Notes

Reaction equation

HRID 1875466 reaction equation
S(Cl)([Cl:3])=O.O[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[N:8][C:7]=1[C:16]([O:18][CH3:19])=[O:17]>>[Cl:3][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[N:8][C:7]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178499158HCID 178499158, compound

Product 1

HCID 20187472Methyl 4-chlorocinnoline-3-carboxylate

Procedure

Thionyl chloride (8.15 g, 5 ml) was added dropwise under inert atmosphere to methyl 4-hydroxycinnoline-3-carboxylate (0.50 g, 2.45 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature and excess thionyl chloride was removed under vacuum. Toluene (5 ml) was added to the residue. The mixture was stirred at room temperature overnight. The solids were collected by filtration and dried under vacuum. The title compound was isolated as a brown solid (248 mg, 1.11 mmol, 45%). LCMS: m/z 223 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. customexcess thionyl chloride was removed under vacuum
  4. additionToluene (5 ml) was added to the residue
  5. filtrationThe solids were collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7a68a5a8db6e467db81839c9be13058d
Source dataset
uspto-grants-2012_11
Patent number
US08309552B2

Reaction notes

Loading…