Phosphorus oxychloride → Ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate

HRID 720500Notes

Reaction equation

HRID 720500 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:18][Cl:19])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8](=O)[NH:9]2)=[CH:4][C:3]=1[O:20][CH3:21].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:8]1[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]([CH2:18][Cl:19])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([O:20][CH3:21])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21892028HCID 21892028, compound

Product 1

HCID 21891992Ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate

Procedure

A suspension of ethyl 7-chloro-4-(chloromethyl)-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate (116.7 g, 50 mmol) in phosphoryl chloride (100 ml) is heated to reflux for 6 hours. The phosphoryl chloride is distilled off. The residue is taken up in water and agitation is carried out for 30 min. The precipitate is filtered out and washed with water until neutrality. The precipitate is taken up in dichloromethane and with a saturated solution of sodium chloride. After filtering through a bed of celite the filtrate is decanted. The organic phase is washed again with a saturated solution of sodium chloride, followed by drying over magnesium sulphate, filtering and evaporating under reduced pressure. 15.88 g of a brown oil is obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. distillationThe phosphoryl chloride is distilled off
  4. filtrationThe precipitate is filtered out
  5. washwashed with water until neutrality
  6. filtrationAfter filtering through a bed of celite the filtrate
  7. customis decanted
  8. washThe organic phase is washed again with a saturated solution of sodium chloride
  9. dry with materialby drying over magnesium sulphate
  10. filtrationfiltering
  11. customevaporating under reduced pressure

Sources & evidence

ORD record
ord-f8c491d31c46404792e1a8c9e939fef3
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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