Triethylamine → Ethyl 2-ethoxy-6-(4-(hydroxymethyl)imidazole-1-yl)-7-nitroquinoline-3-carboxylate

HRID 412068Notes

Reaction equation

HRID 412068 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:20]([O-:22])=[O:21])=[C:9](F)[CH:10]=2)[N:5]=1)[CH3:2].Cl.[OH:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:20]([O-:22])=[O:21])=[C:9]([N:29]3[CH:30]=[C:26]([CH2:25][OH:24])[N:27]=[CH:28]3)[CH:10]=2)[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18536723Ethyl 2-ethoxy-6-fluoro-7-nitroquinoline-3-carboxylateHCID 178418488HCID 178418488, compound

Product 1

HCID 9864967Ethyl 2-ethoxy-6-(4-(hydroxymethyl)imidazole-1-yl)-7-nitroquinoline-3-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 2-ethoxy-6-fluoro-7-nitroquinoline-3-carboxylate (1.00 g, 3.24 mmol) in acetonitrile (10 ml) were added 4-(hydroxymethyl)imidazole hydrochloride (2.18 g, 16.2 mmol) and successively triethylamine (3 ml), and the mixture was stirred for 16 hours at 120° C. in a sealed tube under shading. After cooling, solvent was distilled off and the residue was submitted to silica gel column chromatography [dichloromethane-methanol(50:1→20:1)] under shading to obtain 583 mg of title compound as light brown powder. Yield 47%. 1H-NMR(DMSO-d6, δ): 1.35(3H,t,J=7.3 Hz), 1.42(3H,t,J=7.3 Hz), 4.38 (2H,q,J=7.3 Hz), 4.42(2H,d,J=6.8 Hz), 4.58(2H,d,J=7.3 Hz), 5.05(1H, t,J=5.4 Hz), 7.27(1H,s), 7.88(1H,s), 8.39(1H,s), 8.50(1H,s), 8.87 (1H,s).

Workup

  1. temperatureAfter cooling
  2. distillationsolvent was distilled off

Sources & evidence

ORD record
ord-b5eff1d5cb5e44c386b88c64248013f6
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Reaction notes

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