Triethylamine → 2-chloro-3-nitro-N-prop-2-ynylquinolin-4-amine

HRID 606038Notes

Reaction equation

HRID 606038 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[Cl:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14](Cl)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.C(N(CC)CC)C>ClCCl>[Cl:5][C:6]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([NH:4][CH2:1][C:2]#[CH:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 862475782-chloro-3-nitro-N-prop-2-ynylquinolin-4-amineYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propargylamine (25 mL, 0.36 mol) was added dropwise over a period of five minutes to a 4.5° C. solution of 2,4-dichloro-3-nitroquinoline (84.4 g, 0.347 mol) and triethylamine (73 mL, 0.52 mol) in dichloromethane (1.2 L). After one hour, the solution was allowed to warm to room temperature. After several days, the solvent was evaporated under reduced pressure and the resulting solid was triturated with water and isolated by filtration. The solid was rinsed with water and toluene (500 mL), then was dissolved in dichloromethane and toluene and concentrated under reduced pressure to remove residual water. The solid was dissolved in methanol and ether and concentrated under reduced pressure to afford 2-chloro-3-nitro-N-prop-2-ynylquinolin-4-amine as yellow-brown solid (79.5 g) that contained some impurities and was used without further manipulation.

Workup

  1. waitAfter several days
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting solid was triturated with water
  4. customisolated by filtration
  5. washThe solid was rinsed with water and toluene (500 mL)
  6. dissolutionwas dissolved in dichloromethane
  7. concentrationtoluene and concentrated under reduced pressure
  8. customto remove residual water
  9. dissolutionThe solid was dissolved in methanol
  10. concentrationether and concentrated under reduced pressure

Sources & evidence

ORD record
ord-24f2dadb72f5464e946d430b70aca3a8
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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