Pyridine → Methyl 4-(3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate

HRID 387861Notes

Reaction equation

HRID 387861 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[Cl:28].N1C=CC=CC=1.O1CCCC1.Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:42]>O>[Cl:28][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:2]=1[NH:1][C:41]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:42])[O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 8028TetrahydrofuranHCID 15891Phenyl chloroformate2×HCID 22936947Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Product 1

HCID 58931268Methyl 4-(3-chloro-4-[(phenoxycarbonyl)amino]phenoxy}-7-(2-methoxyethoxy)-6-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate (3.2 g), pyridine (0.71 ml) and tetrahydrofuran (50 ml) were stirred while cooling on ice, and then 1.1 ml of phenyl chloroformate was added dropwise. After 40 minutes, 0.8 ml of pyridine and 1.1 ml of phenyl chloroformate were added and the mixture was stirred for an additional 10 minutes. Water was added, extraction was performed with ethyl acetate, and the extract solution was passed through a glass filter coated with silica gel. The silica gel was washed with ethyl acetate, the solvent was distilled off under reduced pressure, hexane and ethyl acetate were added to the residue and the solid was filtered out to obtain 3.2 g of a faint red solid.

Workup

  1. temperaturewhile cooling on ice
  2. extractionextraction
  3. filtrationfilter
  4. washThe silica gel was washed with ethyl acetate
  5. distillationthe solvent was distilled off under reduced pressure, hexane and ethyl acetate
  6. additionwere added to the residue
  7. filtrationthe solid was filtered out

Sources & evidence

ORD record
ord-2d656cf6e27c4d368cef214383bb0a95
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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