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

HRID 989344Notes

Reaction equation

HRID 989344 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-5ba700de3a0949408425f35b46cbb269
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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