p-Toluenesulfonic acid → HCID 21956390, compound

HRID 2213831Notes

Reaction equation

HRID 2213831 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:18][CH3:19])=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:22][N:23](/[CH:25]=[N:1]/[C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:18][CH3:19])=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1)[CH3:24]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 78373Dimethylformamide dimethyl acetalHCID 21956428HCID 21956428, compound

Product 1

HCID 21956390HCID 21956390, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-amino-6,7-dimethoxy-3-quinolinecarboxylate (3.60 g, 13.04 mmol) and 4.10 g of dimethylformamide dimethylacetal in 60 mL of toluene containing 40 mg of p-toluenesulfonic acid is heated at reflux for 2 hours. Upon cooling to room temperature a solid formed and is collected by filtration to provide 736 mg of methyl 2-{[(E)-(dimethylamino)methylidene]amino}-6,7-dimethoxy-3-quinolinecarboxylate as an off-white solid, mp 166–168° C. MS 318.1, 319.0 (M+H)+ Analysis for C16H19N3O4 Calcd: C, 60.56; H, 6.03; N, 13.24. Found: C, 60.63; H, 6.08; N, 13.32.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. customformed
  4. filtrationis collected by filtration

Sources & evidence

ORD record
ord-6642b54af82449d1809e45d1d5c1d4b1
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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