4-(Methylthio)aniline → HCID 22466681, compound

HRID 612203Notes

Reaction equation

HRID 612203 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:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>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:31][C:30]1[CH:32]=[CH:33][C:27]([S:26][CH3:25])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 660384-(Methylthio)anilineHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466681HCID 22466681, compoundYield 95.2%

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 12 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 181.0 mg (1.3 mmol) of 4-(methylmercapto)-aniline to give 334.1 mg (95.2%) of the product as a yellow solid, m.p. 235-237° C., mass (electrospray, m/e): M+H 351.9, 352.9, 353.8, 354.9.

Sources & evidence

ORD record
ord-472bc7950bbc4488ab5aab99b802e4f5
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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