N,N-Dimethylaniline → HCID 57970162, compound

HRID 1666660Notes

Reaction equation

HRID 1666660 reaction equation
NN1CCCC1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=O)[CH:12]=[C:11]2[O:19][CH3:20].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:13]1[CH:12]=[C:11]([O:19][CH3:20])[C:10]2[C:15](=[CH:16][CH:17]=[C:8]([Cl:7])[CH:9]=2)[N:14]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 279461-PyrrolidinamineHCID 67443391HCID 67443391, compound

Product 1

HCID 57970162HCID 57970162, compound

Procedure

Methyl 5-chloro-2-(2-(triphenyl-λ5-phosphanyliden)-acetylamino)benzoate (3.8 g) was heated at 180° C. for 1 h. The reactant was suspended in chloroform and diisopropyl ether. Solids were collected by filtration and dried to obtain 6-chloro-4-methoxyquinoline-2(1H)-one (1.1 g). (3) A mixture of 6-chloro-4-methoxyquinoline-2(1H)-one (1.1 g), N,N-dimethylaniline (1 mL), and phosphorus oxychloride (4 mL) was stirred at 80° C. to 90° C. for 10 h. The reaction solution was added dropwise to ice water and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, followed by addition of silica gel. The desiccant and silica gel were removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 2,6-dichloro-4-methoxyquinoline (1.2 g) as pale yellow crystals.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. additionfollowed by addition of silica gel
  4. customThe desiccant and silica gel were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3fa1690550049bdbd605f85e27e14fa
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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