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

HRID 1904792Notes

Reaction equation

HRID 1904792 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:31]([OH:33])=[O:32])[CH2:27][CH:26]2[C:28]([OH:30])=[O:29])=[CH:21][CH:20]=1)([O-])=O.C(N)CC.[OH-].[Na+].NC(N)=O.Cl>O1CCCC1>[NH2:16][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:31]([OH:33])=[O:32])[CH2:27][CH:26]2[C:28]([OH:30])=[O:29])=[CH:21][CH:20]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1176UreaHCID 7852PropylamineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 128913651-(4-Nitrophenyl)-1,2-cyclopropanedicarboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.1 g of N,N'-dicyclohexylcarbodiimide are added to a solution of 2.5 g of 1-(4-nitrophenyl)-1,2-cyclopropanedicarboxylic acid in 50 ml of tetrahydrofuran and the mixture is stirred for 1 hour at room temperature. A solution of 0.83 ml of propylamine and 10 ml of tetrahydrofuran is then added dropwise at room temperature to the resultant suspension. The mixture is then stirred at room temperature until reaction is complete. The solvent is evaporated off, the residue is taken up in water and 1 equivalent of sodium hydroxide solution, and the precipitated urea is removed by filtration. The filtrate is acidified with 1 equivalent of hydrochloric acid and extracted twice with methylene chloride. The organic phases are washed once with water, dried over magnesium sulfate and concentrated. Recrystallisation of the residue from ethyl acetate/ether/petroleum ether affords white crystals of the title compound (b) with m.p. 154°-155° C. and Rf=0.45 on thin-layer silica gel plates in the system methylene chloride/methanol/glacial acetic acid (40:5:1).

Workup

  1. stirringThe mixture is then stirred at room temperature until reaction
  2. customThe solvent is evaporated off
  3. extractionextracted twice with methylene chloride
  4. washThe organic phases are washed once with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customRecrystallisation of the residue from ethyl acetate/ether/petroleum ether

Sources & evidence

ORD record
ord-da52b5c6815d47478aba15512c0b2c9d
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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