Ammonia → 2-Hydroxy-4-benzyloxybenzamide

HRID 322943Notes

Reaction equation

HRID 322943 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:20]>C(O)C.CO>[OH:19][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][C:12]=1[C:13]([NH2:20])=[O:14]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 220102682-Hydroxy-4-benzyloxybenzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-benzyloxy-2-hydroxybenzoate (20 g) and concentrated aqueous ammonia (30 mL) in ethanol (100 mL) is heated on the steam bath in a sealed pressure vessel overnight. The contents of the pressure vessel are dissolved in methanol and the solution is evaporated to dryness. The residue is subjected to flash chromatography, eluting first with dichloromethane to remove unreacted starting material, and then with a mixture of ethyl acetate and dichloromethane (3:7 v/v), to obtain 2-hydroxy-4-benzyloxybenzamide (4 g), in the form of a white solid.

Workup

  1. temperatureis heated on the steam bath in a sealed pressure vessel overnight
  2. customthe solution is evaporated to dryness
  3. washeluting first with dichloromethane
  4. customto remove unreacted
  5. additionwith a mixture of ethyl acetate and dichloromethane (3:7 v/v)

Sources & evidence

ORD record
ord-5822f9ac896b402380646c2589de7114
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…