Ammonium Hydroxide → HCID 178510284, compound

HRID 2213792Notes

Reaction equation

HRID 2213792 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]=[C:17]([O:19]C)[CH:16]=[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]=[C:17]([OH:19])[CH:16]=[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 21956465HCID 21956465, compound

Product 1

HCID 178510284HCID 178510284, compound

Conditions

Temperature
215 °C

Procedure

According to the procedure of example 105, the reaction mixture of 373.9 mg (0.954 mmol) of 4-(2,4-dichloroanilino)-8-methoxybenzo[g]quinoline-3-carbonitrile and 10 g of pyridine hydrochloride is stirred at 215° C. for 1 hour under N2. 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 333.4 mg (92.6%) of 4-(2,4-dichloroanilino)-8-hydroxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp 267–269° 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-3d37c625c47e4d778171fe5118aab7c2
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

Loading…