Ethanol → HCID 54735420, compound

HRID 1459450Notes

Reaction equation

HRID 1459450 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[Cl:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][NH:16][C:17]2[N:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=O)=[CH:13][CH:12]=1.C(=O)(O)[O-:30].[Na+].[Na].[CH2:35](O)[CH3:36]>ClCCl.O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[C:17]3[C:18](=[CH:23][CH:24]=[CH:25][N:26]=3)[C:19]([OH:21])=[C:3]([C:4]([O:5][CH2:35][CH3:36])=[O:30])[C:7]2=[O:8])=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 702Ethanol2×HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 109209242-Ethylpropanedioyl dichlorideHCID 54392002Methyl 2-[[(4-chlorophenyl)methyl]amino]-3-pyridinecarboxylate

Product 1

HCID 54735420HCID 54735420, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution ethyl malonyl chloride (3.11 ml) in dichloromethane (11 ml) was added dropwise to a mixture of methyl 2-(4-chlorobenzylamino)nicotinate (5.00 g) and sodium bicarbonate (1.80 g) in dichloromethane (27 ml) at 10° C. under nitrogen. The mixture was boiled under reflux for 6 hours and then left to stand at ambient temperature for 18 hours. The mixture was boiled for a further 6 hours then left to stand at ambient temperature for 64 hours. Water (100 ml) was added and the mixture was stirred at ambient temperature for 45 minutes. The organic layer was separated, washed with 5% hydrochloric acid, then with water, then dried and evaporated to give a residue which was dissolved in ethanol (50 ml) and added dropwise at 10° C. to a solution of sodium (0.58 g) in ethanol (40 ml). The mixture was heated to 95° C. and stirred at this temperature for 30 minutes, then left to stand at ambient temperature for 18 hours. The solvent was removed under reduced pressure and the residue was stirred with 5% hydrochloric acid (250 ml) at 0° C. for 1 hour. The mixture was filtered to give a solid which was recrystallised from ethanol to give ethyl 1-(4-chlorobenzyl)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate, m.p. 142°-144° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. waitleft
  3. waitThe mixture was boiled for a further 6 hours
  4. waitthen left
  5. waitto stand at ambient temperature for 64 hours
  6. customThe organic layer was separated
  7. washwashed with 5% hydrochloric acid
  8. dry with materialwith water, then dried
  9. customevaporated
  10. customto give a residue which
  11. temperatureThe mixture was heated to 95° C.
  12. stirringstirred at this temperature for 30 minutes
  13. waitleft
  14. waitto stand at ambient temperature for 18 hours
  15. customThe solvent was removed under reduced pressure
  16. stirringthe residue was stirred with 5% hydrochloric acid (250 ml) at 0° C. for 1 hour
  17. filtrationThe mixture was filtered
  18. customto give a solid which
  19. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-84b0b21aa70143abb454a42bd32c1cb6
Source dataset
uspto-grants-1998_12
Patent number
US05854257

Reaction notes

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