Acetic Acid → MLS000737573

HRID 2269715Notes

Reaction equation

HRID 2269715 reaction equation
[CH3:1][OH:2].[N+:3]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O)([O-:5])=[O:4].C[C:15](C)([C:19]([O-:21])=[O:20])C([O-])=O.N1CCCC[CH2:24]1.[C:29](O)(=[O:31])C>>[N+:3]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[C:15]([C:19]([O:21][CH3:24])=[O:20])[C:1]([O:31][CH3:29])=[O:2])([O-:5])=[O:4]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 6946994Dimethylmalonat

Product 1

HCID 277385MLS000737573

Procedure

A methanol (300 ml) solution of o-nitrobenzaldehyde (103.1 g), dimethylmalonate (90.1 g), acetic acid (1.2 ml) and piperidine (12 ml) was heated under reflux for 25 hours. The reaction mixture was concentrated. Water was added to the mixture, which was extracted with ethylacetate. The organic layer was washed with 1N hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were washed with IPE to give the entitled compound (59.79 g). The mother liquor was further purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2). The obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (34.13 g).

Workup

  1. temperatureunder reflux for 25 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionWater was added to the mixture, which
  4. extractionwas extracted with ethylacetate
  5. washThe organic layer was washed with 1N hydrochloric acid, water
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated
  8. customThe obtained crude crystals
  9. washwere washed with IPE

Sources & evidence

ORD record
ord-719546471bed4ee7b47cd57e513c7527
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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