Isobutylamine → 4-Isobutylamino-3-nitroquinoline

HRID 255515Notes

Reaction equation

HRID 255515 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17]>O1CCCC1>[CH2:15]([NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 109993104-Isobutylamino-3-nitroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 50.0 g (0.24 mole) of 4-chloro-3-nitroquinoline in 300 ml of tetrahydrofuran was added, in small portions, 52.7 g (0.72 mole) of isobutylamine. The mixture was heated at its reflux temperature for one hour and was then evaporated in vacuo. Water was added to the residue, and the solid was separated by filtration. The solid was suspended in one liter of water, and was dissolved by the gradual addition of concentrated hydrochloric acid (to pH 3 to 4) followed by filtration of the solution. The filtrate was basified (to pH 9 to 10) by the addition of concentrated ammonium hydroxide to provide bright yellow 4-(isobutylamino)-3-nitroquinoline, m.p. 119°-121° C. The structural assignment was supported by infrared spectral analysis.

Workup

  1. temperatureThe mixture was heated at its
  2. temperaturereflux temperature for one hour
  3. customwas then evaporated in vacuo
  4. additionWater was added to the residue
  5. customthe solid was separated by filtration
  6. dissolutionwas dissolved by the gradual addition of concentrated hydrochloric acid (to pH 3 to 4)
  7. filtrationfollowed by filtration of the solution
  8. additionby the addition of concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-2c9e10e44a1f42c88f1009f784c75f84
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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