Triethylamine → HCID 69506750, compound

HRID 2366740Notes

Reaction equation

HRID 2366740 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.Cl.[NH2:23][CH2:24][C:25]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:23][CH2:24][C:25]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 57447126HCID 57447126, compound

Product 1

HCID 69506750HCID 69506750, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-3-nitroquinoline (10.96 g, 52.5 mmol) in dichloromethane (200 mL) was cooled to approximately 0° C., and triethylamine (22.0 mL, 158 mmol) and a solution of ethyl 1-(aminomethyl)cyclohexanecarboxylate hydrochloride (11.65 g, 52.5 mmol) in dichloromethane (30 mL) were sequentially added. The reaction was stirred for four hours, and the solvent was removed under reduced pressure. The residue was stirred in deionized water (50 mL) for one hour, and the mixture was extracted several times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange oil was purified by chromatography on silica gel (eluting with 3-5% methanol in dichloromethane) to provide 11.72 g of ethyl 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanecarboxylate as art orange oil that solidified upon standing.

Workup

  1. customthe solvent was removed under reduced pressure
  2. stirringThe residue was stirred in deionized water (50 mL) for one hour
  3. extractionthe mixture was extracted several times with dichloromethane
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting orange oil was purified by chromatography on silica gel (eluting with 3-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1955af41a30244138bdc3b124f0f9cc3
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…