Acetic Acid → 1,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one

HRID 1700143Notes

Reaction equation

HRID 1700143 reaction equation
N(=[C:3]1[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[NH:5][C:4]1=[O:16])[N:12]=[CH:11][CH:10]=[CH:9]3)N.[O-]CC.[Na+].C(O)(=O)C>O>[CH2:3]1[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[NH:5][C:4]1=[O:16])[N:12]=[CH:11][CH:10]=[CH:9]3

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 178514317HCID 178514317, compound

Product 1

HCID 219070851,3-Dihydro-pyrrolo[3,2-f]quinoline-2-oneYield 33.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution 1.8 g (8.5 mmol) of 1-hydrazono-1,3-dihydropyrrolo[3,2-f]quinolin-2-one in 50 ml of freshly prepared 0.5 M sodium ethoxide solution was stirred at reflux for 3 h. The solution was diluted with 50 ml of water, neutralized with acetic acid, and concentrated on a rotary evaporator until cloudy. The solution was stored in a refrigerator overnight. The solid was filtered off, and the filtrate was extracted with three 80-ml portions of EtOAc. A solution of the solid in MeOH/EtOAc was combined with the extracts and passed through a short pad of silica gel, eluting with EtOAc. The solution was then concentrated to a small volume on a rotary evaporator, and the resulting suspension was diluted with an equal volume of ethanol, sonicated, and filtered to give 3-H-pyrrolo[3,2-f]quinoline-2-one as a light green solid (0.52 g, 33%);

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated on a rotary evaporator until cloudy
  3. customwas stored in a refrigerator overnight
  4. filtrationThe solid was filtered off
  5. extractionthe filtrate was extracted with three 80-ml portions of EtOAc
  6. washeluting with EtOAc
  7. concentrationThe solution was then concentrated to a small volume on a rotary evaporator
  8. additionthe resulting suspension was diluted with an equal volume of ethanol
  9. customsonicated
  10. filtrationfiltered

Sources & evidence

ORD record
ord-f8824e68069e4ef6953b7864db5f1e5e
Source dataset
uspto-grants-2002_02
Patent number
US06350747B1

Reaction notes

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