Hydrochloric Acid → HCID 19599427, compound

HRID 1458620Notes

Reaction equation

HRID 1458620 reaction equation
[CH2:1]1[CH2:9][CH:8]=[CH:7][C:6]2[N:5]3[CH2:10][CH2:11][CH2:12][CH2:13][C:4]3=[C:3]([C:14]([O:16]CC)=[O:15])[C:2]1=2.Cl>C(O)C.[OH-].[Na+]>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[C:3]([C:14]([OH:16])=[O:15])=[C:4]1[CH2:13][CH2:12][CH2:11][CH2:10][N:5]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19599443HCID 19599443, compound

Product 1

HCID 19599427HCID 19599427, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 6,7,8,9-tetrahydro-1 H-pyrido[1,2-a]indole-10-carboxylate (1.20 g, 0.0047 mole) in ethanol (50 ml) and 10% NaOH solution (50 ml) was heated under reflux for 4 hours. The reaction was then acidified with 1M HCl acid (50 ml) and extracted with ethyl acetate (50 ml). The organic layer was separated and extracted with 10% Na2CO3 solution (120 ml) and the aqueous solution then re-acidified with 5M HCl acid and extracted into ethyl acetate (2×75 ml). The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo to afford the title compound (D3) as a white solid (400 mg, 40%).

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionextracted with ethyl acetate (50 ml)
  3. customThe organic layer was separated
  4. extractionextracted with 10% Na2CO3 solution (120 ml)
  5. extractionthe aqueous solution then re-acidified with 5M HCl acid and extracted into ethyl acetate (2×75 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66305e530ae44031b852896fd337a18b
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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