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

HRID 63549Notes

Reaction equation

HRID 63549 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×

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 (200 ml) was added sodium hydroxide (30.8 g, 0.77 mol). The mixture was heated to reflux for 2 hours before being cooled to room temperature and diluted with water (2.64 L). The mixture was then washed with dichloromethane (2×300 ml) and the aqueous layer was acidified with concentrated hydrochloric acid to pH 1.0. The precipitate formed was collected by filtration, washed with water and dried to yield 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid as a dark yellow solid (23 g, 85%). 1H NMR (DMSO-d6) 400 MHz δ: 11.95 (brs, 1H), 7.96 (s, 1H), 7.69 (d, 1H, J=8.4 Hz), 7.06 (t, 1H, J=6.8 Hz), 6.92 (d, 1H, J=6.8 Hz), 4.19 (t, 2H, J=6 Hz), 2.91 (t, 2H, J=6 Hz), 2.11 (t, 2H, J=5.6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. washThe mixture was then washed with dichloromethane (2×300 ml)
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b13c439d656d452abe438d67246057fd
Source dataset
uspto-grants-2016_09
Patent number
US09447088B2

Reaction notes

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