Sulfuric acid magnesium salt (1:1) → HCID 89657464, compound

HRID 521408Notes

Reaction equation

HRID 521408 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=[O:6].O=[C:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[C:18](OC)=[O:19].[O-]S([O-])(=O)=O.[Mg+2]>CO.Cl>[O:19]=[C:18]1[C:3]2[C:4]([C:5]([OH:7])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:13]2[CH2:17][CH2:16][CH2:15][C:14]1=2

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 89657464HCID 89657464, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of methyl 3-aminobenzoate (302 mg, 2.0 mmol) and methyl 2-oxocyclopentanecarboxylate (284 mg, 2.0 mmol) in MeOH (10 mL) were added MgSO4 (240 mg) and concentrated HCl (2 drops), the mixture was heated to 60° C. for 4.0 h. After cooling to room temperature, the solvent was evaporated in vacuum. The mixture was filtered and washed with EtOAc (15 mL), the solvent was evaporated and used for the next step without further purification. The crude mixture was dissolved in PPA (4.0 mL), and was stirred in 130° C. for 3 h. After cooling to the room temperature, water (20 mL) was added, and the mixture was extracted with EtOAc (50 mL×3). The organic layers were combined, dried over Na2SO4, and concentrated to afford the mixture, which was purified on Pre-HPLC to afford 9-oxo-2,3,4,9-tetrahydro-1H-cyclopenta[b]quinoline-8-carboxylic acid as a white solid. MS (ESI) m/e [M+1]+230.0

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated in vacuum
  3. filtrationThe mixture was filtered
  4. washwashed with EtOAc (15 mL)
  5. customthe solvent was evaporated
  6. customused for the next step without further purification
  7. dissolutionThe crude mixture was dissolved in PPA (4.0 mL)
  8. temperatureAfter cooling to the room temperature, water (20 mL)
  9. additionwas added
  10. extractionthe mixture was extracted with EtOAc (50 mL×3)
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated
  13. customto afford the mixture, which
  14. customwas purified on Pre-HPLC

Sources & evidence

ORD record
ord-ad811b43d7a942e5a5638be894312078
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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