Hydrochloric Acid → 1-(4-Aminophenyl)-1,2-cyclopropanedicarboxylic acid

HRID 1904790Notes

Reaction equation

HRID 1904790 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]([OH:18])=[O:17])[CH2:12][CH:11]2[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-].[Na+]>C(O)C.[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]([OH:18])=[O:17])[CH2:12][CH:11]2[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 128913651-(4-Nitrophenyl)-1,2-cyclopropanedicarboxylic acid

Product 1

HCID 200380431-(4-Aminophenyl)-1,2-cyclopropanedicarboxylic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

20 g of 1-(4-nitrophenyl)-1,2-cyclopropanedicarboxylic acid are dissolved in 200 ml of ethanol and the solution is hydrogenated in the presence of 5% palladium on carbon. The suspension so obtained is diluted with methanol and the precipitated product is dissolved by addition of 1 equivalent of methanolic hydrochloric acid. A part of the solvent is stripped off in vacuo, then 1 equivalent of 2N sodium hydroxide solution is added and the mixture is evaporated to dryness. The residue is crystallised from water and dried in vacuo over KOH pellets at 60° C. The title compound (b) is obtained in the form of light brown crystals with a melting point above 230° C. and Rf=0.55 on thin-layer silica gel plates in the system methylene chloride/glacial acetic acid (20:10:2).

Workup

  1. customThe suspension so obtained
  2. customthe mixture is evaporated to dryness
  3. customThe residue is crystallised from water
  4. dry with materialdried in vacuo over KOH pellets at 60° C

Sources & evidence

ORD record
ord-074ce6e883e84e209878527d821407a9
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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