Methyl iodide → Methyl 2-amino-5-(propan-2-yloxy)benzoate

HRID 1070401Notes

Reaction equation

HRID 1070401 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17]I.OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[CH3:17][O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[NH2:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 127191892-Amino-5-(propan-2-yloxy)benzoic acidHCID 86586342HCID 86586342, compound

Product 1

HCID 13052308Methyl 2-amino-5-(propan-2-yloxy)benzoateYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-isopropoxy-2-amino-benzoic acid (806 mg) in DMF (10 mL) was added 60% in oil NaH (182 mg, 4.53 mmol) at 0-5° C. under an argon atmosphere. The ice bath was removed and the mixture was stirred for 40 min at room temperature. After addition of methyl iodide (0.33 mL, 5.45 mmol) the mixture was stirred at room temperature for an additional 6 h. 10% KHSO4/Na2SO4 was added and the mixture was extracted, washed with brine, dried (Na2SO4), and concentrated to dryness. Purification by chromatography gave 114 mg of 5-isopropoxy-2-amino-benzoic acid methyl ester.

Workup

  1. customThe ice bath was removed
  2. stirringwas stirred at room temperature for an additional 6 h
  3. extractionthe mixture was extracted
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-c77e9a02071f455a8348f80f04503007
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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