Sulfuric Acid → Methyl 7-amino-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate

HRID 715967Notes

Reaction equation

HRID 715967 reaction equation
S(=O)(=O)(O)O.CC(C)(C)C([NH:10][C:11]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][CH2:22][CH2:23][CH:16]3[CH2:15][CH2:14][C:13]=2[C:12]=1[C:24]([O:26][CH3:27])=[O:25])=O>CO>[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][CH2:22][CH2:23][CH:16]3[CH2:15][CH2:14][C:13]=2[C:12]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70983965Methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate2×

Product 1

HCID 86712117Methyl 7-amino-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylateYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sulphuric acid (5 mL) was added carefully to a solution of methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate (Intermediate 34, 0.820 g) in methanol (50 mL) and and the resultant mixture was stirred and heated at reflux for 4 hours then left at room temperature for 4 days. The mixture was then heated at reflux for a further 1.5 hours. After cooling the solution was evaporated in vacuo and the residue was partitioned between ethyl acetate and water and basified with 20% aqueous sodium hydroxide solution. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give methyl 7-amino-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoline-6-carboxylate (0.580 g) as a yellow gum.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for a further 1.5 hours
  5. temperatureAfter cooling the solution
  6. customwas evaporated in vacuo
  7. customthe residue was partitioned between ethyl acetate and water
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated in vacuo
  11. customThe residue was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

Sources & evidence

ORD record
ord-00016b1e6f1442fd967b0a4ca410d024
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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