Hydrochloric Acid → HCID 57742166, compound

HRID 660313Notes

Reaction equation

HRID 660313 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[OH:15].N[C:17](N)=[O:18].O.Cl>CN(C=O)C>[O:18]=[C:17]1[NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=2[O:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1176UreaHCID 12370790HCID 12370790, compound

Product 1

HCID 57742166HCID 57742166, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Ethyl 2-(4-amino-3-hydroxyphenyl)propanoate (205 mg, 0.978 mmol) in DMF (5 mL) was added urea (305 mg, 5.19 mmol) and refluxed for 5 hrs. The reaction mixture was cooled to room temperature and added water (30 mL). The mixture was acidified with conc. HCl (1 ml) and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant.

Workup

  1. temperaturerefluxed for 5 hrs
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-fcbddd790caa4124aaa6d16dcf4623fd
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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