Hydrochloric Acid → 4-Bromo-2-(isopropylamino)benzoic acid

HRID 2220368Notes

Reaction equation

HRID 2220368 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](F)[CH:3]=1.[CH:12]([NH2:15])([CH3:14])[CH3:13].Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:15][CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 248246474-Bromo-2-(isopropylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromo-2-fluorobenzoic acid (1 g) in pyridine (5 ml) was added isopropylamine (1.94 ml) at room temperature and the mixture was stirred at 100° C. overnight. The mixture was poured into aqueous hydrochloric acid (1N) and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4-bromo-2-(isopropylamino)benzoic acid (218 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a811718d96444249a7f8081e939d62b4
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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