Pyridinium chloride → 4-[(5-Chloro-2-hydroxyphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

HRID 612196Notes

Reaction equation

HRID 612196 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].[ClH:18].N1C=CC=CC=1.[NH2:25][C:26]1[C:31](Cl)=[CH:30][CH:29]=[CH:28][C:27]=1[OH:33]>C(OCCO)C>[Cl:18][C:30]1[CH:29]=[CH:28][C:27]([OH:33])=[C:26]([NH:25][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:31]=1

Participants

5

Reactant 3

HCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrileHCID 198289622-Amino-3-chlorophenol

Product 1

HCID 53288594-[(5-Chloro-2-hydroxyphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrileYield 91.9%

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 172.3 mg (1.2 mmol) of 2-amino-chlorophenol to give 326.4 mg (91.9%) of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 355.8.

Sources & evidence

ORD record
ord-6fc98159b2134017892e89fd4437c5a3
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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