Lithium Hydroxide → 1-(Carboxymethyl)-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 861482Notes

Reaction equation

HRID 861482 reaction equation
C[O:2][C:3]([CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:21]([F:24])([F:23])[F:22])=[C:13]([N:16]3[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:14]=2)[NH:9][C:8](=[O:25])[C:7]1=[O:26])=[O:4].[OH-].[Li+]>O1CCCC1.O>[C:3]([CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:21]([F:24])([F:23])[F:22])=[C:13]([N:16]3[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:14]=2)[NH:9][C:8](=[O:25])[C:7]1=[O:26])([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 220970571-(Methoxycarbonylmethyl)-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 102474741-(Carboxymethyl)-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 g (5.45 mmol) of 1-(methoxycarbonylmethyl)-7-(1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione (Example 24) were dissolved in 30 ml of tetrahydrofuran, and 0.4 g (16.4 mmol) of lithium hydroxide dissolved in 4 ml of water was added. The mixture was stirred at room temperature for 16 h and then organic solvent was removed under reduced pressure. The aqueous phase was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was recrystallized from methanol, resulting in 1.3 g (69%) of the product. Melting point 161°-163° C. (decomposition).

Workup

  1. additionwas added
  2. customorganic solvent was removed under reduced pressure
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-f42b68a4b7d74f7c91e4090586998089
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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