4-Isobutylamino-3-nitroquinoline → N4-(2-methylpropyl)quinoline-3,4-diamine

HRID 1789436Notes

Reaction equation

HRID 1789436 reaction equation
[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[N+:16]([O-])=O)[CH:2]([CH3:4])[CH3:3]>C1(C)C=CC=CC=1.[Pt]>[NH2:16][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:6]=1[NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 1

HCID 109993104-Isobutylamino-3-nitroquinoline

Product 1

HCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamineYield 100.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

4-Isobutylamino-3-nitroquinoline (31.5 g, 0.1284 moles) from Step (A) above, was dissolved in 300 ml of toluene, and about one g of platinum on charcoal was added thereto. The resulting mixture was hydrogenated on a Parr apparatus for one and one-half hours. The mixture was then heated and filtered. Toluene was removed from the filtrate by rotary evaporation to provide 27.8 g of crude 3-amino-4-(isobutylamino)quinoline. Recrystallization twice from ethyl acetate/hexane provided 18.8 g of purified product, m.p. 98°-100° C. Analysis: Calculated for C13H17N3 : % C, 72.5; % H, 8.0; % N, 19.5; Found: % C, 73.2; % H, 7.8; % N, 19.7.

Workup

  1. temperatureThe mixture was then heated
  2. filtrationfiltered
  3. customToluene was removed from the filtrate by rotary evaporation

Sources & evidence

ORD record
ord-32844ea9b2634382ab9882881a5458d7
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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