Nitric Acid → HCID 22072743, compound

HRID 1490325Notes

Reaction equation

HRID 1490325 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17]([CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][CH:21]=1)=[O:18])(=[O:3])[CH3:2].[N+:30]([O-])([OH:32])=[O:31].O>C(O)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17]([CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31])=[O:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 22072757HCID 22072757, compound

Product 1

HCID 22072743HCID 22072743, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 200 g of 2-(2-acetamidoethyl)-4,4', 5,5'-tetramethoxydeoxybenzoin in 2000 ml of acetic acid was slowly added 60 ml of 70% nitric acid at 0° C. Immediately after the addition, the mixture was poured into water and extracted with methylene chloride. The extract was neutralized with a sodium hydrogencarbonate aqueous solution and washed with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure, and the residue was recrystallized from ethanol to yield 196 g of the title compound.

Workup

  1. customat 0° C
  2. additionImmediately after the addition
  3. extractionextracted with methylene chloride
  4. washwashed with a saturated sodium chloride aqueous solution
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-25865eab34284ada837794c9f11d0227
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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