Ammonium Hydroxide → 4-(2,4-Dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile

HRID 989346Notes

Reaction equation

HRID 989346 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:21]#[N:22].Cl.N1C=CC=CC=1.[OH-].[NH4+]>>[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:21]#[N:22]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 219563924-(2,4-Dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 219564804-(2,4-Dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile

Conditions

Temperature
215 °C

Procedure

A reaction mixture of 566.5 mg (1.44 mmol) of 4-(2,4-dichloroanilino)-7-methoxybenzo[g]quinoline-3-carbonitrile and 10 g of pyridine hydrochloride is stirred at 215° C. for 50 min under nitrogen. After cooling, the mixture is neutralized with 40 mL of a 3% ammonium hydroxide solution and stirred for 0.5 hour. The separated solid is filtered off and washed with water and ether. After drying in vacuo, this yields 527.9 mg (96.5%) of 4-(2,4-dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile as a salmon color solid, mp>300° C.

Workup

  1. temperatureAfter cooling
  2. stirringstirred for 0.5 hour
  3. filtrationThe separated solid is filtered off
  4. washwashed with water and ether
  5. customAfter drying in vacuo

Sources & evidence

ORD record
ord-90151e72988648c6ae3457cf8af9d2ee
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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