Sodium Carbonate → 4-(3-Hydroxy-4-methyl-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

HRID 612154Notes

Reaction equation

HRID 612154 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:24]=[C:23]([OH:25])[C:22]([CH3:26])=[CH:21][CH:20]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:25][C:23]1[CH:24]=[C:19]([NH:18][C:2]2[C:11]3[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=3[O:12][CH3:13])[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:20]=[CH:21][C:22]=1[CH3:26]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 178185-Amino-2-methylphenolHCID 101298981-EthoxyethanolHCID 224665354-Chloro-5,8-dimethoxyquinoline-3-carbonitrile

Product 1

HCID 224666594-(3-Hydroxy-4-methyl-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrileYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.148 g of 4-chloro-5,8-dimethoxy-3-quinolinecarbonitrile, 0.087 g of 5-amino-o-cresol, and 5 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 50 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, dried, and washed with 10 ml of hexanes-ethyl acetate (4:1) to give 0.168 g of 4-(3-hydroxy-4-methyl-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 240-242° C.; mass spectrum (EI, m/e): M 335.1260.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. washwashed with 10 ml of hexanes-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-70197e4b7bec4ec6913c7d265c4d27c2
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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