Trimethylsilyldiazomethane → HCID 2879154, compound

HRID 248673Notes

Reaction equation

HRID 248673 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])[CH2:3][CH2:2]1.[CH3:19][Si](C=[N+]=[N-])(C)C>CO.CCCCCC>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:19])=[O:12])=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 34058094-(Morpholin-4-yl)-3-nitrobenzoic acid

Product 1

HCID 2879154HCID 2879154, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

4-Morpholino-3-nitrobenzoic acid prepared in the same manner as in Example 10(1) (3.0 g) is dissolved in methanol (15 ml), and thereto is added dropwise a 10% solution of trimethylsilyldiazomethane in n-hexane in an equimolar amount, and the mixture is stirred at room temperature for one hour. Methanol is distilled off under reduced pressure, and the residue is extracted with ethyl acetate. The extract is washed with 5% aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure to give methyl 4-morpholino-3-nitrobenzoate (3.2 g).

Workup

  1. distillationMethanol is distilled off under reduced pressure
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe extract is washed with 5% aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order
  4. dry with materialdried over anhydrous sodium sulfate, and ethyl acetate
  5. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-93d06ca6080145e8adfccf32b748acb8
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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