O-Xylene → 4-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 1901959Notes

Reaction equation

HRID 1901959 reaction equation
[NH2:1][C:2]1[C:3]([Cl:18])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:19]1(C)C(C)=CC=CC=1>C(OC(OCC)OCC)C>[Cl:18][C:3]1[C:2]2[N:1]=[CH:19][N:12]([CH2:13][C:14]([CH3:15])([CH3:17])[OH:16])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 7237O-XyleneHCID 226726541-((3-Amino-2-chloroquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol (5 g from EXAMPLE 13) in xylene (50 mL) and triethylorthoformate (5 mL) was heated at 80° C. until no starting material remained as determined by thin layer chromatography. The resulting solution was cooled, and the precipitated product was isolated by filtration and washed with xylene (3×10 mL).

Workup

  1. temperatureThe resulting solution was cooled
  2. customthe precipitated product was isolated by filtration
  3. washwashed with xylene (3×10 mL)

Sources & evidence

ORD record
ord-fb94399504324f79b99b2f8d3a2030df
Source dataset
uspto-grants-1996_11
Patent number
US05578727

Reaction notes

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