Ammonium Hydroxide → HCID 178510285, compound

Reaction equation

[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19]C)[C:16]([O:21]C)=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:23]#[N:24].Cl.N1C=CC=CC=1.[OH-].[NH4+]>>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([OH:19])[C:16]([OH:21])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:23]#[N:24]

Participants

Reactant 3

HCID 14923Ammonium Hydroxide

HCID 10176127Pyridinium chloride

HCID 102959004-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 178510285HCID 178510285, compoundYield 51.7%

Procedure

A mixture of 252.6 mg (0.6 mmol) of 4-(2,4-dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile and 5.0 g of pyridine hydrochloride is heated at 215–220° C. for 40 minutes under nitrogen. After cooling, the mixture is neutralized with 3% ammonium hydroxide aqueous solution and stirred for 30 minutes. The precipitate is collected, washed with water and dried in vacuo. The crude product is passed through a short column of silica gel, eluting with a gradient of methylene chloride/methanol 90:10 to 50:50, to provide 122.8 mg (51.7%) of the product as a brown solid, mp>260° C.