2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 11334324, compound

HRID 2245537Notes

Reaction equation

HRID 2245537 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N+:3]=1[O-:11].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N+:3]([O-:11])=[CH:4][C:5]([C:6]([N:34]2[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 531671-MethylpiperazineHCID 114579603-Pyridinecarboxylic acid, 6-chloro-, 1-oxide

Product 1

HCID 11334324HCID 11334324, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Chloronicotinic acid 1-oxide (0.347 g, 2.0 mmol) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.544 g, 2.2 mmol) were mixed in chloroform (8 mL) at 0° C. 1-Methylpiperazine (0.30 g, 3.0 mmol) was added after 5 min and the reaction mixture was stirred for 16 h at room temperature. The solvent was removed in vacuo and the residual oil was purified on a silica gel column using chloroform/methanol/triethylamine, (100:20:1), as the eluent to give 0.18 g, (35% yield) of the title compound as a brownish solid: 1H NMR (DMSO-d6, 400 MHz) δ 8.56 (s, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 3.63 (br s, 2H), 3.39 (br s, 2H), 2.43 (br s, 2H), 2.34 (br s, 2H), 2.25 (s, 3H); MS (EI) m/z 256 and 258 (M++1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residual oil was purified on a silica gel column

Sources & evidence

ORD record
ord-71ca1e1c548d4bfcbcf029f3ef7a6577
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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