Triethylamine → HCID 67041341, compound

HRID 606132Notes

Reaction equation

HRID 606132 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.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[O:32][N:31]=[C:30]([CH2:33][NH2:34])[CH:29]=2)[CH:23]=1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:34][CH2:33][C:30]1[CH:29]=[C:28]([C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)[O:32][N:31]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 23006268HCID 23006268, compound

Product 1

HCID 67041341HCID 67041341, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitroquinoline (2.09 g, 9.99 mmol) and triethylamine (2.10 mL, 15.0 mmol) were sequentially added to a solution of (5-pyridin-3-ylisoxazol-3-yl)methylamine (2.09 g, 9.99 mmol) in dichloromethane, and the solution was stirred overnight at room temperature. The resultant red solution was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with 2% to 5% methanol in dichloromethane) to provide 1.17 g of 3-nitro-N-[(5-pyridin-3-ylisoxazol-3-yl)methyl]quinolin-4-amine as a yellow-orange solid.

Workup

  1. washThe resultant red solution was washed sequentially with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (eluting with 2% to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0a043d4131fc4350ad87e9dd413cd9d6
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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