2,4-Dichloroaniline → 4-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 2213789Notes

Reaction equation

HRID 2213789 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:29]#[N:30]>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:29]#[N:30]

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 24758Sodium hydrideHCID 98351404-Chloro-7-methoxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 219563924-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrileYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the procedure of Example 14, a reaction mixture of 657.8 mg (4.06 mmol) of 2,4-dichloroaniline and 162.4 mg (4.06 mmol) of sodium hydride in 18 mL of anhydrous DMF is stirred at room temperature for 0.5 hour. To the mixture is added 494.0 mg (1.84 mmol) of 4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile. The resulting mixture is heated at 55° C. for 1 hour. After work up, 624.6 mg (86.2%) of 4-(2,4-dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile is obtained as a yellow solid, mp 215–217° C.

Workup

  1. temperatureThe resulting mixture is heated at 55° C. for 1 hour

Sources & evidence

ORD record
ord-6e7ea2a547484294a6ca20d6d8ae6d07
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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