Triethylamine → HCID 67041255, compound

HRID 606127Notes

Reaction equation

HRID 606127 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.[CH2:22]([C:26]1[O:30][N:29]=[C:28]([CH2:31][NH2:32])[CH:27]=1)[CH2:23][CH2:24][CH3:25]>ClCCl>[CH2:22]([C:26]1[O:30][N:29]=[C:28]([CH2:31][NH:32][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH:27]=1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 45117974HCID 45117974, compound

Product 1

HCID 67041255HCID 67041255, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitroquinoline (1.35 g, 6.48 mmol) and triethylamine (1.36 mL, 9.73 mmol) were sequentially added to a solution of (5-butylisoxazol-3-yl)methylamine (1.00 g, 6.48 mmol) in dichloromethane, and the solution was stirred for 48 hours at room temperature. The volatiles were removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 3% methanol in dichloromethane) to provide 1.33 g of N-[(5-butylisoxazol-3-yl)methyl]-3-nitroquinolin-4-amine as a yellow, crystalline solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel (eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1727338f3919412c9499a8b00410d431
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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