Benzenamine, 4-chloro-2-methoxy- → HCID 22466616, compound

HRID 1935166Notes

Reaction equation

HRID 1935166 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.Cl[C:26]1[CH:33]=[C:30]([O:31][CH3:32])[C:29]([NH2:34])=[CH:28][CH:27]=1>C(OCCO)C>[Cl:18][C:27]1[CH:26]=[CH:33][C:30]([O:31][CH3:32])=[C:29]([NH:34][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:28]=1

Participants

5

Reactant 3

HCID 7143Benzenamine, 4-chloro-2-methoxy-HCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466616HCID 22466616, compoundYield 65%

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 12 mL of 2-ethoxyethanol and in the presence of 115.6 mg (1 mmol) of pyridine hydrochloride was reacted with 189.1 mg (1.2 mmol) of 5-chloro-o-anisidine to give 240.5 mg (65.0%) of the product as a cream solid, m.p. 200-202° C., mass (electrospray, m/e): M+H 369.9, 371.8.

Sources & evidence

ORD record
ord-af92ece6a0054fab979258c9d366105e
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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