3-Chloro-4-methylaniline → 4-[(3-Chloro-4-methylphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

HRID 1935164Notes

Reaction equation

HRID 1935164 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.[Cl:25][C:26]1[CH:31]=[C:30]([NH2:32])[CH:29]=[CH:28][C:27]=1[CH3:33]>C(OCCO)C>[Cl:25][C:26]1[CH:31]=[C:30]([NH:32][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])[CH:29]=[CH:28][C:27]=1[CH3:33]

Participants

5

Reactant 3

HCID 72553-Chloro-4-methylanilineHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 53288614-[(3-Chloro-4-methylphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrileYield 99.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in EXAMPLE 367, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile in 10 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 170.0 mg (1.2 mmol) of 2-chloro-4-amino-toluene to give 350.9 mg (99.4%) of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 353.9, 355.8.

Sources & evidence

ORD record
ord-ec217dce41be45349742cfac631bbd02
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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