HCID 57970082, compound → HCID 67443391, compound

HRID 1666659Notes

Reaction equation

HRID 1666659 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:34])[CH:14]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=O>C(Cl)(Cl)Cl.C(OC(C)C)(C)C>[Cl:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:34])[CH:14]=[C:7]2[O:9][CH3:10]

Participants

4

Reactant 1

HCID 57970082HCID 57970082, compound

Product 1

HCID 67443391HCID 67443391, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7914Diisopropyl EtherSolvent

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. filtrationSolids were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-03bb7e95af7f48678a04bf7a3e91b447
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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