Hydrochloric Acid → 2-Amino-5-(propan-2-yl)benzoic acid

HRID 1725868Notes

Reaction equation

HRID 1725868 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.O.[OH-].[Li+].Cl>C1COCC1.O>[NH2:4][C:5]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 127501112-(Acetylamino)-5-(1-methylethyl)benzoic acid

Product 1

HCID 125621272-Amino-5-(propan-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 2B (0.621 g, 2.81 mmol) and lithium hydroxide monohydrate (0.38 g, 9.0 mmol) in THF (6 mL) and water (6 mL) was stirred at 60° C. for 72 hours, acidified to pH 3.5 with 1M HCl, and extracted twice with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% TFA to provide the desired product. MS (ESI(+)) m/e 180 (M+H)+; (ESI(−)) m/e 178 (M−H)−.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% TFA

Sources & evidence

ORD record
ord-c4628c146d214e22821e3d0a42ed2569
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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