Phosphorus oxychloride → 4-Chloro-5,7-dimethoxyquinoline

HRID 573414Notes

Reaction equation

HRID 573414 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[CH:6]=[CH:7][NH:8]2.C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:5]1[C:4]2[C:9](=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:3]=2[O:2][CH3:1])[N:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 435320065,7-Dimethoxy-1,4-dihydroquinolin-4-one

Product 1

HCID 178804724-Chloro-5,7-dimethoxyquinoline

Procedure

5,7-dimethoxy-1H-quinolin-4-one (300 mg, 1.4 mmol) in POCl3 (5 mL) was heated to reflux for 15 h. The reaction mixture was cooled to rt and poured into ice-water. The mixture was then basified to pH 7 with NaHCO3 and stirred overnight. The solid was filtered and washed with water and dried to give 4-chloro-5,7-dimethoxyquinoline. LCMS m/z=224 (M+1); 1H NMR (CDCl3) δ: 8.56 (d, 1H, J=4.4 Hz), 7.23 (d, 1H, J=4.4 Hz), 7.05 (s, 1H), 6.58 (s, 1H), 3.93 (s, 6H).

Workup

  1. temperatureto reflux for 15 h
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-fe6573202ac347409da15bc3a9562ff0
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

Loading…