4-Chloro-2-fluoroaniline → 4-(4-Chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 612190Notes

Reaction equation

HRID 612190 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])=[C:19]([F:24])[CH:18]=1

Participants

5

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 10176127Pyridinium chlorideHCID 224667634-Chloro-6-methoxy-quinoline-3-carbonitrile

Product 1

HCID 224666024-(4-Chloro-2-fluoro-phenylamino)-6-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

The method of Example 281 was used with 218.6 mg (1 mmol) of 4-chloro-6-methoxy-3-quinolinecarbonitrile, 174.7 mg (1.2 mmol) of 4-chloro-2-fluoro-aniline and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol. This afforded 319.8 mg of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 325.9, 327.9

Sources & evidence

ORD record
ord-7228de8d5d1f4fa494675b83045b4ed4
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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