Hydrochloric Acid → 4-(3-Hydroxy-2-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 1935168Notes

Reaction equation

HRID 1935168 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].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[C:20]=1[CH3:26].Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[OH:25][C:21]1[C:20]([CH3:26])=[C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 1044482-Amino-o-cresolHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224666454-(3-Hydroxy-2-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 51.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.123 g of 3-amino-o-cresol, 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 0.174 g of 4-(3-hydroxy-2-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, mp 255-257° C.; mass spectrum (electrospray, m/e): M+H 335.9.

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-a1febee84c2b46b5ad6de43435c50b84
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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