Methanol → Methyl 4-(aminomethyl)benzoate

HRID 2036784Notes

Reaction equation

HRID 2036784 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.OS(O)(=O)=O.[OH-].[Na+].[CH3:19]O>C(OCC)(=O)C>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:19])=[O:8])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 571728Methyl 4-(aminomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(aminomethyl)benzoic acid (1 g, 7 mmol) in MeOH (10 mL) was added dropwise concentrated H2SO4 (1 mL). Upon completion of addition, the reaction mixture was heated to 60° C. where it stirred for 12 h. After this time, the reaction mixture was concentrated under reduced pressure to yield a residue. The residue was dissolved in ethyl acetate and then carefully neutralized with a 10% NaOH solution. The organic layer was separated and washed successively with water and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford methyl 4-(aminomethyl)benzoate (2.5 g) as a white solid. LCMS Method O: retention time 0.49 min, [M+1]=166.2.

Workup

  1. additionUpon completion of addition
  2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
  3. customto yield a residue
  4. customThe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-634315ea7c0040958d8e70f0c27c14fa
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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