4-Chloro-2-fluoroaniline → HCID 22466584, compound

HRID 612183Notes

Reaction equation

HRID 612183 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]([Cl:31])[CH:28]=[CH:27][C:25]=1[NH2:26]>C(OCCO)C>[Cl:31][C:29]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])=[C:24]([F:23])[CH:30]=1

Participants

5

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 10176127Pyridinium chlorideHCID 224666994-Chloro-8-methoxyquinoline-3-carbonitrile

Product 1

HCID 22466584HCID 22466584, compoundYield 87.9%

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 328.0 mg (1.5 mmol) of 4-chloro-8-methoxy -3-quinolinecarbonitrile, 173.3 mg (1.5 mmol) of pyridine hydrochloride and 240.0 mg (1.7 mmol) of 2-fluoro-4-chloroaniline in 15 mL of 2-ethoxyethanol was heated at 100° C. for 2 hr. After the work up, 431.3 mg (87.9%) of the product was obtained as an off white solid, m.p. 127° C. (dec.), mass spectrum (electrospray, m/e): M+H 327.8, 329.9.

Sources & evidence

ORD record
ord-e324f5ea628a4c2194c06f00b6c45ad3
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…