Sodium Bicarbonate → 1,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one

HRID 1387409Notes

Reaction equation

HRID 1387409 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12](NN)=O.[C:16](=O)(O)[O-:17].[Na+]>Cl>[CH2:12]1[C:3]2=[C:4]3[C:9](=[CH:10][CH:11]=[C:2]2[NH:1][C:16]1=[O:17])[N:8]=[CH:7][CH:6]=[CH:5]3

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 451169886-Aminoquinoline-5-carbohydrazide

Product 1

HCID 219070851,3-Dihydro-pyrrolo[3,2-f]quinoline-2-oneYield 45%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-Aminoquinoline-5-carboxylic acid hydrazide was dissolved in 10 mL of 2 M hydrochloric acid and heated briefly on a hot plate. The reaction was neutralized by gradual addition of solid sodium bicarbonate and filtered. The collected product was dried under vacuum at 55° C. to give 416 mg (45%) of 1,3-dihydro-pyrrolo[3,2-f]quinoline-2-one as a brown solid. Mass spectrum (negative ion chemical ionization): m/z=183 (60%). 1H NMR (DMSO-d6): δ3.80 (s, 2H), 7.35 (d, J=8.8 Hz, 1H), 7.44 (dd, J=8.4, 4.2 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 8.70 (dd, J=4.2, 1.6 Hz, 1H), 10.57 (br s, 1H).

Workup

  1. temperatureheated briefly on a hot plate
  2. filtrationfiltered
  3. customThe collected product was dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-81925f3c01cc43e6885ea720ae8fe3c0
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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