Acetone → 3-Acetylamino-4-methoxy-6-(4-nitrobenzoyl)-phenylacetone

HRID 2179900Notes

Reaction equation

HRID 2179900 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[O:10][CH:9]([CH3:26])[CH2:8]2)(=[O:3])[CH3:2].CC(C)=[O:29]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:8][C:9](=[O:29])[CH3:26])[C:12]([C:11](=[O:10])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[CH:13][C:14]=1[O:15][CH3:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 180AcetoneHCID 224889656-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Product 1

HCID 697343163-Acetylamino-4-methoxy-6-(4-nitrobenzoyl)-phenylacetoneYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of compound 14 (0.375 g, 1.05 mmol) in 30 ml of acetone was added 3 ml of CrO3 in 35% H2SO4 at 0° C. The resulted solution was stirred another 2 h at same temperature. Ice water was added. The solution was extracted with ethyl acetate three times. The combined organic phase was washed with brine, followed by drying over Na2SO4. Removal of the solvent afforded the desired product in the yield of 82%. 1HNMR(CDCl3): 8.5-7.8 (m, 6H), 6.8 (s, 1H), 4.08 (s, 2H), 3.8 (s, 3H), 2.24 (s, 3H), 2.21 (s, 3H).

Workup

  1. extractionThe solution was extracted with ethyl acetate three times
  2. washThe combined organic phase was washed with brine
  3. dry with materialby drying over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-0033ab1111e34e1c9d3eb25bd809485c
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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