Sodium Hydroxide → HCID 66817569, compound

HRID 1754974Notes

Reaction equation

HRID 1754974 reaction equation
[OH-].[Na+].C([N:6]([C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([Br:21])=[C:16]([CH3:22])[CH:15]=1)[CH2:7][CH2:8][O:9]C(=O)CBr)(=O)C>CCO.C(OCC)(=O)C>[Br:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([NH:6][CH2:7][CH2:8][OH:9])=[CH:15][C:16]=1[CH3:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86672766HCID 86672766, compound

Product 1

HCID 66817569HCID 66817569, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6 N NaOH (1.5 ml) was added to a solution of bromo-acetic acid 2-[acetyl-(4-bromo-3,5-dimethyl-phenyl)-amino]-ethyl ester (302 mg, 0.74 mmol) in EtOH (6 ml). The reaction solution was heated under reflux overnight, cooled to room temperature and then diluted with ethyl acetate. The organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-(4-bromo-3,5-dimethyl-phenylamino)-ethanol (181 mg, 68%).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux overnight
  3. washThe organic phase was sequentially washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2fb478297b574e2f84dc69e401f985e1
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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