2,4,6-Trifluoroaniline → 8-Methoxy-4-(2,4,6-trifluoro-phenylamino)-quinoline-3-carbonitrile

HRID 1935101Notes

Reaction equation

HRID 1935101 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].Cl.N1C=CC=CC=1.[F:23][C:24]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[C:25]=1[NH2:26]>C(OCCO)C>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([C:14]#[N:15])=[C:2]2[NH:26][C:25]1[C:24]([F:23])=[CH:30][C:29]([F:31])=[CH:28][C:27]=1[F:32]

Participants

5

Reactant 3

HCID 677652,4,6-TrifluoroanilineHCID 10176127Pyridinium chlorideHCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 224666418-Methoxy-4-(2,4,6-trifluoro-phenylamino)-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 274. A reaction mixture of 200.0 mg (0.92 mmol) of 4-chloro-8-methoxy-3-quinolinecarbonitrile, 105.7 mg (0.92 mmol) of pyridine hydrochloride and 148.6 mg (1.0 mmol) of 2,4,6-trifluoro-aniline in 10 mL of 2-ethoxyethanol was heated at 100° C. for 2 hr. The work up gave 112.6 mg (37.4%) of the product as a yellow solid, m.p. 297° C. (dec.), mass spectrum (electrospray, m/e): M+H 330.0.

Sources & evidence

ORD record
ord-a6b86180ff65470dad23ab513d9f0429
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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