Triethylamine → HCID 15224452, compound

HRID 991929Notes

Reaction equation

HRID 991929 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.[NH2:23][CH2:24][C:25]([CH3:29])([OH:28])[CH:26]=[CH2:27]>C(Cl)Cl>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:23][CH2:24][C:25]([CH3:29])([OH:28])[CH:26]=[CH2:27])[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 125552251-Amino-2-methyl-but-3-en-2-ol

Product 1

HCID 15224452HCID 15224452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyl amine (6.2 mL, 0.045 mole) was added to a solution of 2,4-dichloro-3-nitroquinoline (10.9 g 0.045 mole) in methylene chloride (60 mL). 4-Amino-3-methyl-1-butene-3-ol was added and the reaction mixture was heated at reflux for several hours before being concentrated under vacuum. The residue was chilled in an ice bath to give a solid. The solid was recrystallized from toluene to provide 17.1 g of the desired product as a yellow solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for several hours
  3. concentrationbefore being concentrated under vacuum
  4. temperatureThe residue was chilled in an ice bath
  5. customto give a solid
  6. customThe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-3d1d4c6b3d3a48579fd3b31a4b156423
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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