3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoroanilino)benzo[g]quinoline-3-carbonitrile

HRID 2213717Notes

Reaction equation

HRID 2213717 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[F:26])[NH2:22].Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[F:26])[NH:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 98346304-Chlorobenzo[g]quinoline-3-carbonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 99681424-(3-Chloro-4-fluoroanilino)benzo[g]quinoline-3-carbonitrileYield 77.9%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 3, the reaction mixture of 141.8 mg (0.60 mmol) of 4-chlorobenzo[g]quinoline-3-carbonitrile, 87.3 mg (0.60 mmol) of 3-chloro-4-fluoroaniline and 57.8 mg (0.50 mmol) of pyridine hydrochloride in 8.0 mL of 2-ethoxyethanol is heated at 110–120° C. for 1 hour to yield 162.5 mg (77.9%) of the product as a bright yellow solid, mp 257–259° C.

Workup

  1. temperatureis heated at 110–120° C. for 1 hour

Sources & evidence

ORD record
ord-eaf5fd146fd342e9b82bf364b70a60dc
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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