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

HRID 557160Notes

Reaction equation

HRID 557160 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-3678052c0c3740a8a7e3b32ebefc9e24
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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