Pyridine → HCID 22466722, compound

HRID 612185Notes

Reaction equation

HRID 612185 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].N1C=CC=CC=1.Cl.[CH3:23][N:24]([CH3:32])[C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>C(OCCO)C>[CH3:23][N:24]([CH3:32])[C:25]1[CH:26]=[C:27]([NH:28][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12646050N~1~,N~1~-Dimethylbenzene-1,3-diamine--hydrogen chloride (1/1)HCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 22466722HCID 22466722, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 274. A reaction mixture of 250.0 mg (1.1 mmol) of 4-chloro-8-methoxy -3-quinolinecarbonitrile, 273.3 mg (3.0 mmol) of pyridine and 261.4 mg (1.25 mmol) of 3-dimethylaminoaniline hydrochloride in 10 mL of 2-ethoxyethanol was heated at 100° C. for 1.5 hr. The work up gave 294.8 mg (73.4%) of the product as a deep greenish yellow solid, m.p. 222-225° C., mass spectrum (electrospray, m/e): M+H 319.0.

Sources & evidence

ORD record
ord-d219b97ef36f46f98af753347edc02e7
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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