3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

HRID 2213722Notes

Reaction equation

HRID 2213722 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:20]#[N:21].[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])[NH2:26].Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])[NH:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 99441164-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 101361054-(3-Chloro-4-fluoroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrileYield 90.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 11, a mixture of 149.4 mg (0.50 mmol) of 4-chloro-7,8-dimethoxybenzo[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 7.0 mL of 2-ethoxyethanol is heated at 100–110° C. for 1.0 hour to yield 184.4 mg (83.0%) of the product as a yellow solid, mp>280° C.

Workup

  1. temperatureis heated at 100–110° C. for 1.0 hour

Sources & evidence

ORD record
ord-be9f8329616642cd9ead0c2cae48f19d
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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