Hydrochloric Acid → HCID 19108506, compound

HRID 327441Notes

Reaction equation

HRID 327441 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.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15745000HCID 15745000, compound

Product 1

HCID 19108506HCID 19108506, compoundYield 94.6%

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 mol) 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 HCl (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. Calcd. 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-f806e00f9ef64dc1a3429fc6fe064d10
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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