Hydrochloric Acid → 6,7-Dimethoxy-4-(2-methylsulfanyl-phenylamino)-quinoline-3-carbonitrile

HRID 1935079Notes

Reaction equation

HRID 1935079 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][S:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[S:19][CH3:18]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 763372-(Methylthio)anilineHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224666976,7-Dimethoxy-4-(2-methylsulfanyl-phenylamino)-quinoline-3-carbonitrileYield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.139 g of 2-(methylmercapto)aniline, 20 mg of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrogen chloride to adjust pH to 7. The product was collected, washed with water, and dried to give 0.184 g of 6,7-dimethoxy-4-(2-methylsulfanyl-phenylamino)-quinoline-3-carbonitrile as a solid, mp 245-247° C.; mass spectrum (EI, m/e): M 351.1051.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9f6c49ade58143d0b6a2f28cfbe42a53
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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