Sodium Hydroxide → 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

HRID 983920Notes

Reaction equation

HRID 983920 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][CH2:9][N:8]3[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:6]1([C:4]([OH:5])=[O:3])[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20729414Ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylate

Product 1

HCID 225568865,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid ethyl ester (31 g, 0.14 mol) in ethanol (200 mL) and water (70 mL) was added 5 N aqueous sodium hydroxide (60 mL, 0.3 mol) and the resulting mixture stirred at reflux for 3 hours. The reaction mixture was cooled to 20-24° C., diluted with water (2 L) and washed with dichloromethane (2×200 mL) and diethyl ether (1×200 mL). The aqueous layer was filtered through Celite and the filtrate was acidified with conc. HCl (25 mL) to precipitate the product. The solid was filtered, washed with water (200 mL), and dried in vacuo to give 23.2 g (85%) of the desired compound as a light yellow solid.

Workup

  1. temperatureat reflux for 3 hours
  2. washwashed with dichloromethane (2×200 mL) and diethyl ether (1×200 mL)
  3. filtrationThe aqueous layer was filtered through Celite
  4. customto precipitate the product
  5. filtrationThe solid was filtered
  6. washwashed with water (200 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-58eea256f44549558286333200a3f071
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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