Toluene → 1-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

HRID 1789440Notes

Reaction equation

HRID 1789440 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.C1(C)C=CC=CC=1>[Pt].C(O)C>[NH2:15][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[NH:4][CH2:3][C:2]([OH:1])([CH3:18])[CH3:19])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 1140TolueneHCID 139583422-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

Product 1

HCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Using the method of Example 16, 7.0 g (0.027 mole) of 4-(2-hydroxy-2-methylpropylamino)-3-nitroquinoline, 1 g of platinum on charcoal, 200 ml of toluene and 150 ml of ethanol was hydrogenated on a Paar apparatus. The solution was filtered, then evaporated to dryness to provide 3-amino-4-(2-hydroxy-2-methylpropylamino)quinoline as a solid residue. To the residue was added 50 ml of triethyl orthoformate and 5 drops of formic acid. The solution was heated at 135° to 140° C. for one hour, then allowed to stand for about 16 hours. The product was separated by filtration, dissolved in hydrochloric acid and reprecipitated with sodium hydroxide solution. The product was recrystallized from ethanol to provide 1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline hydrate, m.p. 169°-170° C. Analysis: Calculated for C14H15N3O. H2O: % C, 64.8; % H, 6.6; % N, 16.2; Found: % C, 65.1: % H, 6.6; % N, 16.4.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-688336cc55214556ac93ccfe0ea98ef2
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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