Allylamine → N-allyl-2-chloro-3-nitroquinolin-4-amine

HRID 606032

Reaction equation

HRID 606032 reaction equation
C(N(CC)CC)C.[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.[CH2:23]([NH2:26])[CH:24]=[CH2:25]>ClCCl>[CH2:23]([NH:26][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([Cl:8])[C:18]=1[N+:19]([O-:21])=[O:20])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 59007293N-allyl-2-chloro-3-nitroquinolin-4-amineYield 105.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (17.0 mL, 123 mmol) was added to a 0° C. solution of 2,4-dichloro-3-nitroquinoline (20.0 g, 82.3 mmol) in dichloromethane (350 mL) followed by the dropwise addition of allylamine (5.90 mL, 78.2 mmol). The solution was allowed to stir and warm to room temperature overnight. The solvent was evaporated under reduced pressure and the resulting orange solid was suspended in water (300 mL). Solid sodium carbonate was added to adjust the pH to 10-11 and the suspension was stirred for 2 hours at 0° C. A yellow solid was isolated by filtration and dried under vacuum overnight to yield N-allyl-2-chloro-3-nitroquinolin-4-amine (21.7 g) that contained small amounts of an impurity and water.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionSolid sodium carbonate was added
  3. stirringthe suspension was stirred for 2 hours at 0° C
  4. customA yellow solid was isolated by filtration
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-7533faf04dc6419f89e9b1ab9f5be9e6
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Linked notes

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