Hydrochloric Acid → HCID 19958555, compound

HRID 373769Notes

Reaction equation

HRID 373769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]([CH2:13][C:14]([O:16]CC)=[O:15])[C:7](=[O:19])[CH:6]=[N:5]2.[OH:20]O.Cl>[OH-].[Na+]>[C:14]([CH2:13][N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[C:11]([Cl:12])[CH:10]=2)[NH:5][C:6](=[O:20])[C:7]1=[O:19])([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 19958587HCID 19958587, compound

Product 1

HCID 19958555HCID 19958555, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The above ester (1.5 g, 5 mmol) was suspended in 70 ml of 2.5% NaOH and 30% H2O2 (1.95 ml) was added. The mixture was warmed at 70°-80° C. for 5 h, cooled and acidified (pH=1) with concentrated hydrochloric acid. The precipitate was filtered off and recrystallized from DMF-water to afford 1.17 g (81%) of the title compound. M.p. 317°-19° C. 1H-NMR (DMSO-d6):δ4.95 (s, 2H), 7.36 (s, 1H), 7.72 (s, 1H), 12.13 (s, 1H), 13.32 (br.s, 1H).

Workup

  1. temperatureThe mixture was warmed at 70°-80° C. for 5 h
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. customrecrystallized from DMF-water

Sources & evidence

ORD record
ord-45729c19fb964028a03b4b5725effc1e
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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