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

HRID 989303Notes

Reaction equation

HRID 989303 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].Br.[Br:18][C:19]1[CH:25]=[C:24]([Cl:26])[C:23]([O:27][CH3:28])=[CH:22][C:20]=1[NH2:21].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Br:18][C:19]1[CH:25]=[C:24]([Cl:26])[C:23]([O:27][CH3:28])=[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 10176127Pyridinium chlorideHCID 219564212-Bromo-4-chloro-5-methoxyaniline hydrobromideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

Product 1

HCID 693724308-(2-Bromo-4-chloro-5-methoxy-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrileYield 44.9%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.12 g (0.52 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.2 g (0.63 mmol) of 2-bromo-4-chloro-5-methoxyaniline hydrobromide and 0.06 g (0.52 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 0.1 g of 8-(2-bromo-4-chloro-5-methoxy-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as a yellow solid, mp 257° C. (dec).

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-a6583902099247908369f0fca8949c46
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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