p-Toluenesulfonic acid monohydrate → HCID 10110605, compound

HRID 1934936Notes

Reaction equation

HRID 1934936 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1Cl)=[CH:10][C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=2)#[N:2].[NH2:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Br:25])[CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>COCCO>[Br:25][C:23]1[CH:24]=[C:19]([NH:18][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:1]#[N:2])[CH:20]=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 8176813-Amino-5-bromopyridineHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 10110605HCID 10110605, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
153 °C

Procedure

A mixture of 249 mg (1 mmole) of 3-cyano-4-chloro-6,7-dimethoxy quinoline, 346 mg (2 mmoles) of 3-amino-5-bromo pyridine and 20 mg (about 0.1 mmole) of p-toluenesulfonic acid monohydrate in 5 ml of 2-methoxy ethanol was stirred and refluxed in an oil bath at 153° C. for 7 hours. On cooling overnight to room temperature, the solid was filtered and washed with ethanol, then with ether to give 287 mg (74.5%) of N-[4-[(5-bromo-3-pyridinyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile, which melted at 272-275° C. mass spectrum (electrospray, m/e) M+H=384.9, 386.8.

Workup

  1. temperatureOn cooling overnight to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-94bc6dc9394a4d76820b573c8b2226ab
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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