Phenazopyridine hydrochloride → Phenazopyridine

HRID 2063231Notes

Reaction equation

HRID 2063231 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1[CH:8]=[CH:9][C:10]([N:13]=[N:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:22])=[N:19][C:20]=2[NH2:21])=[CH:11][CH:12]=1.Cl.C(OCC)(=O)C>O>[CH:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:22])=[N:19][C:20]=2[NH2:21])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8691Phenazopyridine hydrochlorideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 4756Phenazopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 27.6 grams (200 mmol) of potassium carbonate in 200 mL of water was added 20.0 grams (80 mmol) of phenazopyridine hydrochloride followed by 200 mL of ethyl acetate. The mixture was stirred at room temperature for 30 minutes. The layers were separated and the aqueous layer was extracted one time with 100 mL of ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, and filtered. The filtrate was concentrated under diminished pressure and the product was dried under vacuum at room temperature to give an orange solid: yield 15.1 grams (92%). 1H NMR (300 MHz, CDCl3) δ 4.80 (br s, 4H), 6.06 (d, 1H), 7.34 (m, 1H), 7.48 (m, 2H), 7.76 (m, 2H), and 7.93 (d, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted one time with 100 mL of ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under diminished pressure
  6. customthe product was dried under vacuum at room temperature
  7. customto give an orange solid

Sources & evidence

ORD record
ord-0c5079e1206b451c8de60eb45ad9c3dc
Source dataset
uspto-grants-2012_10
Patent number
US08288365B2

Reaction notes

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