Water → Methyl 4-amino-2-(3-chloropropoxy)benzoate

HRID 400360Notes

Reaction equation

HRID 400360 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:14][CH2:15][CH2:16][Cl:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 77787Methyl p-aminosalicylate

Product 1

HCID 67284899Methyl 4-amino-2-(3-chloropropoxy)benzoateYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-amino-2-hydroxybenzoate (500 mg, 2.99 mmol) and 1-bromo-3-chloropropane (0.294 mL, 2.99 mmol) in DMF (3 mL) was added CESIUM CARBONATE (1462 mg, 4.49 mmol). The resulting mixture was stirred at 60° C. for 6 hrs. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over MgSO4, concentrated. The crude product was purified by silica gel chromatography using a gradient of 20-50% EtOAc/Hexanes to give 686 mg (94%) methyl 4-amino-2-(3-chloropropoxy)benzoate.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e9365e0cb77445f848d6bb4faae9222
Source dataset
uspto-grants-2014_06
Patent number
US08741884B2

Reaction notes

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