(Benzyloxy)acetic acid → HCID 21188731, compound

HRID 1383957Notes

Reaction equation

HRID 1383957 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:17][CH2:18][C:19](O)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:10]([O:17][CH2:18][C:19]1[NH:8][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([OH:9])[C:2]=2[N:1]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 290301(Benzyloxy)acetic acidHCID 516892Sodium BicarbonateHCID 5799372,3-Diaminophenol

Product 1

HCID 21188731HCID 21188731, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of the 2,3-diaminophenol (5 g, 40.3 mmol, 1 eq) and benzyloxyacetic acid (5.6 g, 48.3 mmol, 1.2 eq) in 40 ml of a 10% aqueous solution of sodium bicarbonate was stirred and refluxed at 140° C. for one hour. The mixture was allowed to cool down to room temperature. Ethyl acetate was poured into the mixture. The organic fraction was extracted with ethyl acetate, washed with water, and then dried over sodium sulfate. The solvents were removed in vacuo. The crude product was further purified by flash chromatography to yield 6.87 grams (67% yield) of the desired title product.

Workup

  1. temperatureto cool down to room temperature
  2. extractionThe organic fraction was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customThe crude product was further purified by flash chromatography

Sources & evidence

ORD record
ord-e9dc6b705aa742c1a4cca9ae31050713
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

Loading…