Lithium hydroxide, monohydrate → 4-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

HRID 1969993Notes

Reaction equation

HRID 1969993 reaction equation
O.[OH-].[Li+].[O:4]=[C:5]1[C:14]2[NH:15][CH:16]=[CH:17][C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.C([C:20]([O-:22])=[O:21])C>C(O)C.O>[O:4]=[C:5]1[C:14]2[NH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86627461HCID 86627461, compound

Product 1

HCID 120650844-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acidYield 101.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.64 g (39 mmol) of lithium hydroxide monohydrate is added to 1 g (3.9 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 1) suspended in 45 mL of ethanol and 45 mL of water, and the solution is stirred for 17 h at 70° C. then 5 h at 100° C. The ethanol is evaporated under vacuum and distilled water is added. The aqueous solution is washed with ethyl acetate then acidified with acetic acid to pH 4-5. The precipitate that forms is filtered then dried under vacuum at 55° C. to give 0.9 g (100%) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a beige solid.

Workup

  1. custom5 h
  2. customat 100° C
  3. customThe ethanol is evaporated under vacuum
  4. distillationdistilled water
  5. additionis added
  6. washThe aqueous solution is washed with ethyl acetate
  7. filtrationThe precipitate that forms is filtered
  8. customthen dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-30b33b656ab94966a4cf89f4cc120d46
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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