Sodium Bicarbonate → 8-(2-Chloro-5-methoxy-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile

HRID 989304Notes

Reaction equation

HRID 989304 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]=[C:8]3[CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]#[N:16].Cl.[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:20]=1[NH2:21].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:20]=1[NH:21][C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]=[C:8]3[CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239002-Chloro-5-methoxyanilinium chlorideHCID 10176127Pyridinium chlorideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

Product 1

HCID 693722158-(2-Chloro-5-methoxy-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrileYield 62.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.2 g (0.87 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.22 g (1.04 mmol) of 2-chloro-5-methoxyaniline hydrochloride and 0.1 g (0.87 mmol) of pyridine hydrochloride in 5.0 mL of 2-ethoxyethanol is heated at reflux temperature for 1 hour, cooled to room temperature, poured into a saturated solution of sodium bicarbonate and stirred for 0.5 hour. The solid is collected by filtration, washed with water and dried. The solid is purified by silica gel chromatography utilizing a gradient of methylene chloride/methanol(97:3 to 90:10) to yield 0.19 g of 8-(2-chloro-5-methoxy-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as beige solid, mp 296-298° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe solid is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a50059c922fe48c6827cea69f1e2a0ac
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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