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

HRID 1725357Notes

Reaction equation

HRID 1725357 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1)=[O:7])C>C(O)C.O>[C:8]1([C:6]([OH:7])=[O:5])[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=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

Add 5 N aqueous sodium hydroxide (60 mL, 0.3 mol) 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) and stir the resulting mixture at reflux for 3 hours. Cool the reaction mixture to 20-24° C., dilute with water (2 L), and wash sequentially with dichloromethane (2×200 mL) and diethyl ether (1×200 mL). Filter the aqueous layer through Celite and treat the filtrate with concentrated hydrochloric acid (25 mL) to precipitate the product. Filter the solid, wash with water (200 mL), and dry under reduced pressure to give the desired compound as a light yellow solid (23.2 g, 85%).

Workup

  1. temperatureat reflux for 3 hours
  2. washwash sequentially with dichloromethane (2×200 mL) and diethyl ether (1×200 mL)
  3. filtrationFilter the aqueous layer through Celite
  4. additiontreat the filtrate with concentrated hydrochloric acid (25 mL)
  5. customto precipitate the product
  6. filtrationFilter the solid
  7. washwash with water (200 mL)
  8. customdry under reduced pressure

Sources & evidence

ORD record
ord-9e22e51bb6214dc8970d7736ac1ce0a0
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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