Water → 4-Aminocoumarin

HRID 26037

Reaction equation

HRID 26037 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C([O-])(=O)C.[NH4+:17].O>C(O)CO>[NH2:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 546829304-Hydroxycoumarin

Product 1

HCID 8208074-AminocoumarinYield 99.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
60 °C

Procedure

97.2 g of 4-hydroxycoumarin and 69.3 g of ammonium acetate in 300 ml of ethylene glycol are heated to 70° C. for 3 hours, whilst stirring, and to 160° C. for 6 hours, the mixture is cooled to 60° C., 1 liter of water is added, whilst stirring, and the mixture is cooled to room temperature. The colourless crystalline precipitate is filtered off, washed with water and dried in vacuo at 60° C. 96 g of 4-aminocoumarin in an almost pure form are obtained

Workup

  1. stirringwhilst stirring
  2. temperaturethe mixture is cooled to room temperature
  3. filtrationThe colourless crystalline precipitate is filtered off
  4. washwashed with water
  5. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-6c8bd853f10e4d0da1191df774022583
Source dataset
uspto-grants-1979_04
Patent number
US04147865

Linked notes

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