Sodium Carbonate → HCID 22466711, compound

HRID 1935062Notes

Reaction equation

HRID 1935062 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]=[C:23]([OH:25])[C:22]([CH3:26])=[CH:21][CH:20]=1.Cl.N1C=CC=CC=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](=[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:20]=[CH:21][C:22]=1[CH3:26]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 178185-Amino-2-methylphenolHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466711HCID 22466711, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.98 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 1.85 g of 5-amino-o-cresol, 1.39 g of pyridine hydrochloride, and 200 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 1 h. The mixture was cooled and added to 1000 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried to give 3.27 g of 4-(3-hydroxy-4-methyl-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, mp 222-224° C.; mass spectrum (EI, m/e): M 335.1269.

Workup

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

Sources & evidence

ORD record
ord-309f32ff882b4c139531912ff548fc83
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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