Toluene → HCID 23498077, compound

HRID 1837352Notes

Reaction equation

HRID 1837352 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[NH:9][CH:8]=[C:7]([C:20]#[N:21])[C:6]2=O.C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:6]1[C:5]2[C:10](=[CH:11][C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][C:7]=1[C:20]#[N:21]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 10108715HCID 10108715, compound

Product 1

HCID 23498077HCID 23498077, compound

Conditions

Temperature
105 °C

Procedure

A reaction mixture of 0.3 g (1.01 mmol) of 6-methoxy-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carbonitrile in 5 mL of phosphorus oxychloride is heated at 105° C. for 45 minutes. After cooling, the mixture is concentrated to dryness in vacuo to give a brown solid. To this is added 5 mL toluene, and the solution is concentrated to dryness again. Dropwise, an ice-cooled saturated aqueous sodium carbonate solution is added to the residue. This mixture is extracted with 5×25 mL of a 95:5 mixture of methylene chloride/methanol. The organic layer is dried over magnesium sulfate. The magnesium sulfate is removed by filtration, and solvent is removed in vacuo to provide 0.255 g of 4-chloro-6-methoxy-7-(4-methylpiperazin-1-yl)-quinoline-3-carbonitrile as a yellow solid, mp 177-179° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness in vacuo
  3. customto give a brown solid
  4. concentrationthe solution is concentrated to dryness again
  5. temperatureDropwise, an ice-cooled saturated aqueous sodium carbonate solution
  6. additionis added to the residue
  7. extractionThis mixture is extracted with 5×25 mL of a 95:5 mixture of methylene chloride/methanol
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. customThe magnesium sulfate is removed by filtration, and solvent
  10. customis removed in vacuo

Sources & evidence

ORD record
ord-7d1fdc8889b64489aab696f9995677fb
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

Loading…