Hydrochloric Acid → HCID 43803194, compound

HRID 886603Notes

Reaction equation

HRID 886603 reaction equation
C([O:3][C:4](=[O:16])[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[N:6]([CH3:8])[CH3:7])C.[OH-].[K+].O.Cl>CN(C=O)C>[Br:15][C:11]1[CH:10]=[C:9]([CH:5]([N:6]([CH3:8])[CH3:7])[C:4]([OH:16])=[O:3])[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 59825088(3-Bromo-phenyl)-dimethylamino-acetic acid ethyl ester

Product 1

HCID 43803194HCID 43803194, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-bromo-phenyl)-dimethylamino-acetic acid ethyl ester (350 mg, 1.2 mmol) in DMF was added potassium hydroxide (4 mL, 50% in water) and water (50 mL). The resulting mixture was refluxed for 25 hours. The mixture was neutralized to pH 7 with concentrated hydrochloric acid and extracted with ethyl acetate (50 mL×4). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford (3-Bromo-phenyl)-dimethylamino-acetic acid (290 mg, 94%). MS: m/z 258 (M+H+).

Workup

  1. temperatureThe resulting mixture was refluxed for 25 hours
  2. extractionextracted with ethyl acetate (50 mL×4)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a42f0df76c642b8b18c4d4975adae2e
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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