Sulfuric Acid → HCID 15338727, compound

HRID 635909Notes

Reaction equation

HRID 635909 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[O:5][C:4]([CH3:16])([CH3:15])[CH2:3]1.S(=O)(=O)(O)O.[C:22](=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:22])=[O:13])[CH:10]=2)[O:5][C:4]([CH3:16])([CH3:15])[CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 15338726HCID 15338726, compound

Product 1

HCID 15338727HCID 15338727, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.05 mol of 4-amino-6-carboxy-2,2-dimethylchroman is treated with 9.5 ml of conc. sulfuric acid in 200 ml of methanol and the dark solution is heated to reflux for 6 hours. The reaction mixture is adjusted to pH 9 with ice cooling by addition in portions of saturated aqueous potassium carbonate solution and the precipitated salt is filtered off. The solvent is distilled off on a rotary evaporator, the oily residue is treated with water and the mixture is extracted several times with diethyl ether. After removing the solvent by distillation, the oily amorphous residue is crystallized under n-heptane.

Workup

  1. temperaturethe dark solution is heated
  2. temperatureto reflux for 6 hours
  3. filtrationthe precipitated salt is filtered off
  4. distillationThe solvent is distilled off on a rotary evaporator
  5. additionthe oily residue is treated with water
  6. extractionthe mixture is extracted several times with diethyl ether
  7. customAfter removing the solvent
  8. distillationby distillation
  9. customthe oily amorphous residue is crystallized under n-heptane

Sources & evidence

ORD record
ord-f11216567c3343a1a9700f3530876bf5
Source dataset
uspto-grants-2001_02
Patent number
US06191164B1

Reaction notes

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