Acetic Acid → 2-Chloro-N~4~-(2-methylpropyl)quinoline-3,4-diamine

HRID 1901953Notes

Reaction equation

HRID 1901953 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)(=O)C.[H][H]>[Pt].C(O)(C)C>[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 109348134-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 117470392-Chloro-N~4~-(2-methylpropyl)quinoline-3,4-diamineYield 73%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 2-chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine (120 g), acetic acid (300 mL), isopropyl alcohol (300 mL), and 5% platinum on carbon (7.2 g) was allowed to stand at room temperature for 30 h under 2 bars of hydrogen pressure. The resulting solution was filtered, and the solvent was removed from the filtrate at reduced pressure. The residue was dissolved in aqueous hydrochloric acid (1 L, 4N). The product was precipitated by adding this solution to a solution of sodium hydroxide. The precipitate was filtered and washed with water to afford the product 2-chloro-N4 -(2-methylpropyl)-3,4-quinolinediamine in 73% yield.

Workup

  1. filtrationThe resulting solution was filtered
  2. customthe solvent was removed from the filtrate at reduced pressure
  3. dissolutionThe residue was dissolved in aqueous hydrochloric acid (1 L, 4N)
  4. customThe product was precipitated
  5. additionby adding this solution to a solution of sodium hydroxide
  6. filtrationThe precipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-efd20eae31894e3fb3fd09663aaedbbc
Source dataset
uspto-grants-1996_11
Patent number
US05578727

Reaction notes

Loading…