Formaldehyde → N-(diethylaminomethyl)-1-(4-fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide

HRID 1032718Notes

Reaction equation

HRID 1032718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([NH2:27])=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.[CH2:28]=O.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>C(O)C>[CH2:30]([N:32]([CH2:28][NH:27][C:25]([C:10]1[C:11](=[O:24])[C:12]2[C:17](=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:9]=1)=[O:26])[CH2:33][CH3:34])[CH3:31]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 4433701-(4-Fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide

Product 1

HCID 492948N-(diethylaminomethyl)-1-(4-fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.2 g 1-(4-fluorophenyl)-1,4-di -hydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide (Example 1h) and molar excess amounts of formaldehyde and diethylamine in 100 ml ethanol was heated at reflux for two days. The ethanol was removed and the residual product chromatographed on silica gel. The column was eluted with 10% isopropyl alcohol in chloroform; starting material was eluted first followed by fractions containing the desired N-diethylaminomethyl compound. The latter was recrystallized from ethyl acetate to give 0.9 g N-(diethylaminomethyl)-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide, m.p. 193195° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. customThe ethanol was removed
  4. customthe residual product chromatographed on silica gel
  5. washThe column was eluted with 10% isopropyl alcohol in chloroform
  6. washstarting material was eluted first
  7. additioncontaining the desired N-diethylaminomethyl compound
  8. customThe latter was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b0be327bba2b4e64acd2db9f82b94f7d
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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