Hydrochloric Acid → 7-Chloro-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid

HRID 910158Notes

Reaction equation

HRID 910158 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([O:13]CC)=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:16])[C:3]=1[CH3:17].C1COCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:16])[C:3]=1[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57689808Ethyl 7-chloro-6-methyl-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Product 1

HCID 576898047-Chloro-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 8c (225 mg, 0.88 mmol) was stirred in a solution of THF (4 mL), MeOH (2 mL), and 1N NaOH (2 mL) at r.t. for 20 h. The solution was made acidic with 1N HCl and extracted (3×) with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo to give 190 mg (95%) of compound 8d as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.16 (s, 1H), 4.01 (t, 2H, J=6.9 Hz), 3.26 (t, 2H, J=7.6 Hz), 1.96-2.17 (m, 5H). MS (ES) [m+H] calc'd for C10H10ClNO3, 228. found 228.

Workup

  1. extractionextracted (3×) with CHCl3
  2. dry with materialOrganics were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b172eea6b5be4e6f95bbc591a4f2b831
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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