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

HRID 606050Notes

Reaction equation

HRID 606050 reaction equation
Cl.[CH2:2]([NH2:7])[CH2:3][CH2:4][C:5]#[CH:6].[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>ClCCl>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:7][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinolineHCID 71353516Pent-4-yn-1-amine--hydrogen chloride (1/1)

Product 1

HCID 862475932-chloro-3-nitro-N-pent-4-ynylquinolin-4-amineYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pent-4-yn-1-amine hydrochloride (5.48 g, 45.8 mmol) was added to a 6° C. solution of 2,4-dichloro-3-nitroquinoline (10.6 g, 43.6 mmol) and triethylamine (15.2 mL, 109 mmol) in dichloromethane (100 mL). After 30 minutes, the solution was allowed to warm to room temperature. After 5 hours, the volatiles were removed under reduced pressure and the solid residue was triturated with water and isolated by filtration. The filter cake was rinsed with water and toluene and was allowed to dry for several days to yield 2-chloro-3-nitro-N-pent-4-ynylquinolin-4-amine as an orange solid (13.16 g).

Workup

  1. waitAfter 5 hours
  2. customthe volatiles were removed under reduced pressure
  3. customthe solid residue was triturated with water
  4. customisolated by filtration
  5. washThe filter cake was rinsed with water and toluene
  6. customto dry for several days

Sources & evidence

ORD record
ord-42b8f4c8f3df43a28b899739ba68945c
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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