Methanol → N-(2-Methoxy-5-nitrophenyl)-4,4-dimethyl-3-oxopentanamide

HRID 1488905Notes

Reaction equation

HRID 1488905 reaction equation
CO[C:3](=[O:11])[CH2:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].[CH3:12][O:13][C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH2:16].CO>C1(C)C=CC=CC=1>[CH3:9][C:6]([CH3:7])([CH3:8])[C:5](=[O:10])[CH2:4][C:3]([NH:16][C:15]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:14]=1[O:13][CH3:12])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 74472-Methoxy-5-nitroanilineHCID 99597Methyl pivaloylacetate

Product 1

HCID 11162196N-(2-Methoxy-5-nitrophenyl)-4,4-dimethyl-3-oxopentanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl-4,4-dimethyl-3-oxovalerate (15.8 g, 0.1 mol) and 2-methoxy-5-nitroaniline (16.8 g, 0.01 mol) were taken up in toluene (150 mL) in a round bottomed flask fitted with a Dean-Stark trap. The mixture was heated to a vigorous reflux while the MeOH side-product was distilled off and removed. After 4 hours, the mixture was cooled and the toluene removed in vacuo. The residue was recrystallized from acetonitrile to yield 27 g of the desired condensation product.

Workup

  1. customfitted with a Dean-Stark trap
  2. temperatureThe mixture was heated to
  3. distillationwas distilled off
  4. customremoved
  5. temperaturethe mixture was cooled
  6. customthe toluene removed in vacuo
  7. customThe residue was recrystallized from acetonitrile
  8. customto yield 27 g of the desired
  9. customcondensation product

Sources & evidence

ORD record
ord-494c3b27ba084c668774250a44afec1e
Source dataset
uspto-grants-1997_10
Patent number
US05677114

Reaction notes

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