Chlorotrimethylsilane → Methyl 4-(aminomethyl)benzoate

HRID 531423Notes

Reaction equation

HRID 531423 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.Cl[Si](C)(C)[CH3:14]>CO>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:14])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 571728Methyl 4-(aminomethyl)benzoateYield 114.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4-(aminomethyl)benzoic acid (1.0 g, 6.61 mmol) and chlorotrimethylsilane (3.35 mL, 26.44 mmol) was stirred for 30 minutes at room temperature, and anhydrous methanol (20 mL) was added thereto. The reaction mixture was stirred for 48 hours and then vacuum distilled to give methyl 4-(aminomethyl)benzoate (1.25 g, 94%). 1H NMR (500 MHz, D2O) δ 8.02 (d, 2H, J=6.4 Hz), 7.51 (d, 2H, J=8.2 Hz), 4.20 (s, 2H), 3.88 (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred for 48 hours
  2. distillationvacuum distilled

Sources & evidence

ORD record
ord-51971328718f4dd5a0500e333d994aa5
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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