Sodium Hydroxide → HCID 19108506, compound

HRID 1648284Notes

Reaction equation

HRID 1648284 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[C:13]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])([C:14]([O:16]CC)=[O:15])[CH2:12][C:11]2=[CH:24][CH:25]=[CH:26][C:9]3=[C:10]2[N:5]1[CH2:6][CH2:7][CH2:8]3>CO>[O:3]=[C:4]1[C:13]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])([C:14]([OH:16])=[O:15])[CH2:12][C:11]2=[CH:24][CH:25]=[CH:26][C:9]3=[C:10]2[N:5]1[CH2:6][CH2:7][CH2:8]3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15745000HCID 15745000, compound

Product 1

HCID 19108506HCID 19108506, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (10 mL of 4.0 N, 0.04 mol) was slowly added to ethyl 2,3,6,7-tetrahydro-3-oxo-2-((1-oxopropyl)amino)-1H,5H-benzo(ij)quinolizine-2-carboxylate (3.33 g, 0.010 tool) in methanol (50 mL). After stirring at room temperature for 30 minutes, the solvent was removed under reduced pressure. The resulting solid was dissolved in water (20 mL) and methanol (trace), neutralized with 4N HC1 (10 mL, 0.04 mol), cooled to -10° C., and the precipitate was filtered off and air dried to give 2.86 g of 2,3,6,7-tetrahydro-3-oxo-2-((1-oxopropyl) amino)-1H,5H-benzo(ij)quinolizine-2-carboxylic acid. This was refluxed in ethanol for 20 minutes to effect decarboxylation. The ethanol was removed under reduced pressure and the solid was crystallized from ethyl acetate:hexane to give 1.85 g of N-(2,3,6,7-tetrahydro-3-oxo-1H, 5H-benzo(ij)quinolizin-2-yl)propanamide, mp 149°-152° C. A sample was recrystallized for analysis; mp 152°-154° C. Anal. Calc'd for C15H18N2O2 : C, 69.74; H, 7.02; N, 10.85. Found: C, 69.33; H, 7.33; N, 10.68.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe resulting solid was dissolved in water (20 mL)
  3. temperaturecooled to -10° C.
  4. filtrationthe precipitate was filtered off
  5. customair dried

Sources & evidence

ORD record
ord-49c2bef1a4754df4af86c3db6ac12585
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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