Sodium Carbonate → 4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 612216Notes

Reaction equation

HRID 612216 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].[Cl:18][C:19]1[C:25]([OH:26])=[CH:24][C:22]([NH2:23])=[C:21]([F:27])[CH:20]=1.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:18][C:19]1[C:25]([OH:26])=[CH:24][C:22]([NH:23][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])=[C:21]([F:27])[CH:20]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 224665744-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.25 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.195 g of 4-chloro-2-fluoro-5-hydroxyaniline, 0.116 g of pyridine hydrochloride, and 3 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 1 h. The mixture was cooled and added to 10 ml of water. To this mixture was added sodium carbonate until pH 9. The product was collected, washed with water, and dried to give 0.327 g of 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, dec >260° C. ; mass spectrum (electrospray, m/e): M+H 373.9.

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-b32853a20d554784b8207a5ef76fb860
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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