Benzene → HCID 22010727, compound

HRID 323133Notes

Reaction equation

HRID 323133 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][OH:19])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C.CN(C)[CH:59]=[O:60]>O.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([O:60][CH3:59])=[O:19])=[O:9])=[CH:21][CH:22]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 241BenzeneHCID 6228DimethylformamideHCID 167693TrimethylsilyldiazomethaneHCID 2724130Cornforth reagentHCID 22010650HCID 22010650, compound

Product 1

HCID 22010727HCID 22010727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-nitro-N-methyl-N-[2-(2-hydroxyethyl)phenyl]benzamide (686 mg) in N,N-dimethylformamide (12 ml) was added pyridinium dichromate (4.3 g) and the mixture was stirred at ambient temperature for 2 days. The mixture was diluted with water (80 ml) and the aqueous solution was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Filtering and removal of solvents afforded a brown oil. To a solution of the brown oil in methanol (3 ml) and benzene (11 ml) was added trimethylsilyl diazomethane (1.7 ml) and the resulting solution was stirred at ambient temperature for 30 minutes. The mixture was evaporated in vacuo to give 4-nitro-N-methyl-N-(2-methoxycarbonylmethylphenyl)benzamide (517 mg) as a dark-green oil.

Workup

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltering
  5. customremoval of solvents
  6. customafforded a brown oil
  7. stirringthe resulting solution was stirred at ambient temperature for 30 minutes
  8. customThe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-ba858072efd54647886a5c18e2ff1fb7
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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