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5-Amino-2-methylphenol → 8-(3-Hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile

HRID 989305
Notes
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Reaction equation

HRID 989305 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].[NH2:17][C:18]1[CH:23]=[C:22]([OH:24])[C:21]([CH3:25])=[CH:20][CH:19]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[OH:24][C:22]1[CH:23]=[C:18]([NH:17][C:2]2[C:11]3[CH:10]=[C:9]4[N:12]=[CH:13][N:14]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:19]=[CH:20][C:21]=1[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

Product 1

HCID 693742998-(3-Hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrileYield 81.7%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.15 g (0.66 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.1 g (0.78 mmol) of 5-amino-o-cresol and 0.075 g (0.66 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, diethyl ether, methylene chloride, tetrahydrofuran and dried in vacuo to yield 0.17 g of 8-(3-hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as white solid, mp 257-260° C. (dec).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationThe solid is collected by filtration
  4. washwashed with water, diethyl ether, methylene chloride, tetrahydrofuran
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b9b323e2db5f44e0b41c4dd8fb5de1d7
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06638929B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes