Hydrochloric Acid → 8-Bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52463Notes

Reaction equation

HRID 52463 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16]([O:18]C)=[O:17])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[OH-].[Na+].Cl>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 104489598-bromo-5-methoxycarbonyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 99955808-Bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dioneYield 108.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-bromo-5-methoxycarbonyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (256 mg, 0.76 mmol) in a mixture of THF (5 mL) and methanol (5 mL) was added aqueous 1N NaOH (2.5 mL) and the mixture was stirred for 12 h at room temperature. Aqueous 1N HCl was added and the resulting mixture was concentrated to ca. 5 mL. The precipitates formed were collected by filtration, washed with distilled water, and dried in vacuo to give 256 mg of the title compound (quant): mp 285° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ13.45 (bs, 1H), 12.09 (s, 1H), 7.22 (d, 1H, J=1Hz), 7.08 (d, 1H, J=1 Hz), 5.18 (dd, 1H, J=11, 4 Hz), 3.79 (dd, 1H, J=17, 11 Hz), 3.33 (dd, 1H, J=17, 4 Hz).

Workup

  1. concentrationthe resulting mixture was concentrated to ca. 5 mL
  2. customThe precipitates formed
  3. filtrationwere collected by filtration
  4. washwashed with distilled water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f4df157a809a410f8ae4ec7fc24464fa
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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