Isobutylamine → 4-Isobutylamino-3-nitroquinoline

HRID 1789413Notes

Reaction equation

HRID 1789413 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.Og (0.24 mole) of 4-chloro-3-nitroquinoline in 300 ml of tetrahydrofuran was added, in small portions, 52.7g (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), at which time the solution was filtered. 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), at which time the solution
  7. filtrationwas filtered
  8. additionby the addition of concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-2a25a670f29446a8bcfed9c8a1b1ea10
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

Loading…