(4-Aminophenoxy)benzene → 6,7-Dimethoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile

HRID 1935165Notes

Reaction equation

HRID 1935165 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.[O:25]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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:36][C:35]1[CH:34]=[CH:33][C:32]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 99781256,7-Dimethoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrileYield 71.3%

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 222.3 mg (1.2 mmol) of 4-phenoxyaniline to give 283.0 mg (71.3%) of the product as a light yellow solid, m.p. 239-241° C., mass (electrospray, m/e): M+H 397.9.

Sources & evidence

ORD record
ord-59ac156333f34ae382bbd355b66ebc67
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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