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Water → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

HRID 1593783
Notes
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Reaction equation

HRID 1593783 reaction equation
[C:1]([C:3](=[CH:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[C:21]([I:30])[CH:20]=1)[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=O)#[N:2].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:16][C:8]1[CH:9]=[C:10]([Cl:15])[C:11]([O:13][CH3:14])=[CH:12][C:7]=1[NH:6][C:4]1[C:24]2[C:19](=[CH:20][C:21]([I:30])=[C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:23]=2)[N:18]=[CH:17][C:3]=1[C:1]#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride3×HCID 693123182-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide

Product 1

HCID 115847334-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrileYield 88.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide (1.0 g, 1.80 mmol) in 35 mL of toluene was heated to reflux and phosphorous oxychloride (1.7 mL, 18.0 mmol) was added dropwise. The mixture was heated at reflux for 2 hours, and an additional 1.7 mL of phosphorous oxychloride was added. The mixture was continued to heat at reflux for 2 hours, and an additional 1.7 mL of phosphorous oxychloride was added and the reaction mixture was heated at reflux overnight. The reaction is then cooled to room temperature and water was added followed by 10 N sodium hydroxide. The mixture was stirred in an ice-bath for 30 minutes and the precipitate was collected by filtration, washed with methylene chloride to give 870 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrile as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 3.41 (s, 3H), 3.81 (t, 2H), 3.87 (s, 3H), 4.34 (t, 2H), 7.40 (s, 1H), 7.78 (s, 1H), 7.88 (s, 1H), 8.43 (s, 1H), 8.45 (s, 1H), 9.85 (s, 1H); MS (ES) m/z542.1, 544.1 (M−H)−

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperatureto heat
  6. temperatureat reflux for 2 hours
  7. temperaturethe reaction mixture was heated
  8. temperatureat reflux overnight
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with methylene chloride

Sources & evidence

ORD record
ord-54a225f9798244bbba87f9588ea8649b
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07297795B2

Reaction notes

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