Hydrochloric Acid → 4-cyclopentyl-5,6-dihydro4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

HRID 500454Notes

Reaction equation

HRID 500454 reaction equation
C([O:3][C:4]([C:6]1[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH:9]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:8]3[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O.C(O)C>[CH:18]1([CH:9]2[CH2:10][CH2:11][C:12]3[C:17]4=[C:16]([C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]24)[CH:15]=[CH:14][CH:13]=3)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 686766484-cyclopentyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid ethyl ester

Product 1

HCID 686748084-cyclopentyl-5,6-dihydro4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acidYield 85.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-cyclopentyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid ethyl ester (1.45 g, 4.9 mmol) in water (10 ml) and ethanol (15 ml) was added sodium hydroxide (1.96 g, 49 mmol) and the reaction mixture heated at reflux overnight (˜14 h). The reaction was cooled and acidifed with 5 M HCl. The resulting white precipitate was filtered and dried in vacuo to give 4-cyclopentyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (1.13 g, 4.2 mmol) as a white solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux overnight (˜14 h)
  3. temperatureThe reaction was cooled
  4. filtrationThe resulting white precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ef7ee6d06c444907bb5faeba78d38214
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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