Diethyl Ether → HCID 21956427, compound

HRID 2213838Notes

Reaction equation

HRID 2213838 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][CH2:19][CH2:20][Cl:21])=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.CO[CH:24](OC)[N:25]([CH3:27])[CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>C1(C)C=CC=CC=1>[Cl:21][CH2:20][CH2:19][O:18][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:2](/[N:1]=[CH:24]/[N:25]([CH3:27])[CH3:26])=[N:3]2)=[CH:8][C:7]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 78373Dimethylformamide dimethyl acetalHCID 21956379HCID 21956379, compound

Product 1

HCID 21956427HCID 21956427, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-amino-7-[2-chloroethoxy]-6-methoxy-3-quinolinecarboxylate (5.00 g, 16.09 mmol) and 5.10 g of dimethylformamide dimethylacetal in 75 mL of toluene containing 50 mg of p-toluenesulfonic acid is heated at reflux for 10 minutes then cooled to room temperature. Diethyl ether is added and the solids are collected by filtration to provide 3.81 g of methyl 7-(2-chloroethoxy)-2-{[(1E)-(dimethylamino)methylidene]amino}-6-methoxy-3-quinolinecarboxylate as a pale yellow solid, mp 108–110° C. MS 366.1, 368.1 (M+H)+ Analysis for C17H20ClN3O4.0.5H2O Calcd. C, 54.47; H, 5.65; N, 11.21. Found: C, 54.86; H, 5.62; N, 10.89.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 10 minutes
  3. filtrationthe solids are collected by filtration

Sources & evidence

ORD record
ord-8c16defc71bb4ec1aa0d5673828d72e6
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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