2,4-Dichloroaniline → HCID 21956465, compound

HRID 989345Notes

Reaction equation

HRID 989345 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]=[C:25]([O:27][CH3:28])[CH:24]=[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]=[C:25]([O:27][CH3:28])[CH:24]=[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 9965241HCID 9965241, compound

Product 1

HCID 21956465HCID 21956465, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the procedure of Example 14, a reaction mixture of 487.7 mg (3.01 mmol) of 2,4-dichloroaniline and 120.6 mg (3.01 mmol) of sodium hydride in 15 mL of anhydrous DMF is stirred at room temperature for 0.5 hour. To the mixture is added 367.0 mg (1.37 mmol) of 4-chloro-8-methoxybenzo[g]quinoline-3-carbonitrile. The resulting mixture is heated at 55° C. for 0.5 hour. After work up, 443.3 mg (82.1%) of 4-(2,4-dichloroanilino)-8-methoxybenzo[g]quinoline-3-carbonitrile is obtained as a yellow solid, mp>260° C.

Workup

  1. temperatureThe resulting mixture is heated at 55° C. for 0.5 hour

Sources & evidence

ORD record
ord-99e95fe69ba144cf924d2b4df77f531e
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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