Hydrochloric Acid → N-(2,3,6,7-tetrahydro-3-oxo-1H,5H-benzo(ij)quinolizin-2-yl)formamide

HRID 327438Notes

Reaction equation

HRID 327438 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[C:13]([NH:19][CH:20]=[O:21])(C(OCC)=O)[CH2:12][C:11]2=[CH:22][CH:23]=[CH:24][C:9]3=[C:10]2[N:5]1[CH2:6][CH2:7][CH2:8]3.Cl>CO>[O:3]=[C:4]1[CH:13]([NH:19][CH:20]=[O:21])[CH2:12][C:11]2=[CH:22][CH:23]=[CH:24][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 86747427HCID 86747427, compound

Product 1

HCID 19919292N-(2,3,6,7-tetrahydro-3-oxo-1H,5H-benzo(ij)quinolizin-2-yl)formamideYield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (5.0 mL of 4.0 N, 20 mmol) was slowly added to ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate (3.04 g, 10.0 mmol) in methanol (25 mL). After stirring at room temperature for 30 min, hydrochloric acid (5.0 mL of 4.0 N) was added and the precipitate was filtered off, washed with water and air dried to give 2.4 g of N-(2,3,6,7-tetrahydro-3-oxo-1H,5H-benzo(ij)quinolizin-2-yl)formamide, mp 149°-152° C. A portion of the product was recrystallized from ethyl acetate for analysis; mp 140°-143°. Anal. Calcd. for C13H14N2O2 : C, 67.81; H, 6.13; N, 12.17. Found: C, 67.67; H, 6.07; N, 11.94.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-a7daa9475a134468afa5fac1ad7bec21
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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