Acetic Acid → HCID 18537637, compound

HRID 1637494Notes

Reaction equation

HRID 1637494 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=1[N+:16]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CO.C(OCC)(=O)C.[Zn]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=1[NH2:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 19348779HCID 19348779, compound

Product 1

HCID 18537637HCID 18537637, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.52 g (84.4 mmol) of zinc powder were added to a suspension of 1.06 g (4.21 mmol) of methyl 2-(4-t-butyl-3-nitrophenyl)acetate [prepared as described in step (i) above] in 30 ml of methanol, and subsequently acetic acid was added to the mixture in four 0.8 ml portions over a period of 1 hour. The reaction mixture was stirred for 2 hours, after which it was diluted with ethyl acetate. It was then filtered using a Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure, and the concentrate was again dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of ammonium chloride, with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 870 mg (yield 94%) of the title compound as an oily substance.

Workup

  1. filtrationIt was then filtered
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  4. dissolutionthe concentrate was again dissolved in ethyl acetate
  5. washThe resulting solution was washed with a saturated aqueous solution of ammonium chloride, with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order
  6. customafter which it was dried
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through 50 g of silica gel
  9. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-fafc419a6e2c46759e7ae9183c3e1c68
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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