Hydrogen Peroxide → HCID 178440937, compound

HRID 1057760Notes

Reaction equation

HRID 1057760 reaction equation
[OH:1]O.[CH2:3]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([OH:15])[N:8]=1)[CH2:4][CH:5]=[CH2:6]>CCO.[OH-].[Na+]>[CH2:3]([C:7]1[CH:14]=[CH:13][C:10]([C:11]([NH2:12])=[O:1])=[C:9]([OH:15])[N:8]=1)[CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 178440933HCID 178440933, compound

Product 1

HCID 178440937HCID 178440937, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Hydrogen peroxide (30 wt. % solution in water, 45 mL) was added to a solution of a1 (12.13 g, 70.2 mmol) in a mixture of EtOH (150 mL) and 10% aqueous NaOH (280 mL) at 23° C. The reaction mixture was heated to 50° C. for 18 h, then was cooled to 23° C. and the volatiles were removed under reduced pressure. The residue was acidified with 12 M HCl to pH 2-3, and the resulting precipitate was filtered, washed with water (2×50 mL), and air-dried to afford b1 as a yellow solid (13.48 g, 100%): mp=195-198° C.; IR (cm−1) 3329, 3134, 1688, 1642; 1H NMR (DMSO-d6) δ 2.31-2.38 (m, 2H), 2.64 (t, 2H, J=7.6), 4.96-5.05 (m, 2H), 5.71-5.84 (m, 1H), 6.29 (d, 1H, J=7.3), 7.45 (s, br, 1H), 8.21 (d, 1H, J=7.3), 9.00 (s, br, 1H), 12.37 (s, br, 1H); Anal. C10H12N2O2·0.15H2O: C, H, N.

Workup

  1. temperaturewas cooled to 23° C.
  2. customthe volatiles were removed under reduced pressure
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water (2×50 mL)
  5. customair-dried

Sources & evidence

ORD record
ord-88de84d4eefc4b03bc5fd8fcb66d97c3
Source dataset
uspto-grants-2003_02
Patent number
US06514997B2

Reaction notes

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