Benzenamine, 3-(methylthio)- → HCID 5328860, compound

HRID 1935112Notes

Reaction equation

HRID 1935112 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.N1C=CC=CC=1.[CH3:25][S:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30]>C(OCCO)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:30][C:29]1[CH:31]=[CH:32][CH:33]=[C:27]([S:26][CH3:25])[CH:28]=1

Participants

5

Reactant 3

HCID 15693Benzenamine, 3-(methylthio)-HCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328860HCID 5328860, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in Example 286, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile in 15 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 167.1 mg (1.2 mmol) of 3-(methylthio)aniline to give 134.1 mg (38.2%) of the product as an off white solid, m.p.>250° C., mass (electrospray, m/e): M+H 351.9.

Sources & evidence

ORD record
ord-89aadfd9231c4e048ab315daa24e10d8
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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