Triethylamine → HCID 68536167, compound

HRID 1992585Notes

Reaction equation

HRID 1992585 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C=O)C.ClCCl>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 13578DiglycolamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 68536167HCID 68536167, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-aminoethoxy)ethanol (30.3 g, 288 mmol) in a minimal amount of dichloromethane was added dropwise to a stirred mixture of 4-chloro-3-nitroquinoline (50.0 g, 240 mmol), potassium carbonate (33.1 g, 240 mmol), and triethylamine (36.4 g mL, 360 mmol) in DMF (200 mL) at 0° C. A yellow precipitate formed and more dichloromethane (several mL) was added. The mixture was allowed to warm to room temperature and stir overnight. A yellow solid was isolated by filtration, washed with water and dichloromethane, and dried. The filtrate was washed twice with brine, dried over magnesium sulfate, and filtered. Additional orange solid was isolated from the filtrate after concentration under reduced pressure. The solids were dried in a vacuum oven to afford 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethanol.

Workup

  1. customA yellow precipitate formed
  2. customA yellow solid was isolated by filtration
  3. washwashed with water and dichloromethane
  4. customdried
  5. washThe filtrate was washed twice with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customAdditional orange solid was isolated from the filtrate
  9. concentrationafter concentration under reduced pressure
  10. customThe solids were dried in a vacuum oven

Sources & evidence

ORD record
ord-f7c2693d5c354630bbd262d8d0834019
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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