Methanol → Methyl 4-(aminomethyl)benzoate hydrochloride

HRID 1020392Notes

Reaction equation

HRID 1020392 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.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:16])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideYield 99%

Procedure

4-Aminomethylbenzoic acid (2.0 g, 13 mmol) was dissolved in MeOH (5.0 mL), thionylchloride (2.9 mL, 3 equiv.) was slowly added thereto at 0° C. and fluxed for 24 hrs. The mixture thus obtained was distilled under a reduced pressure to remove the solvent and thionyl chloride, and dried under vacuum to obtain the title compound (2.7 g, 99%).

Workup

  1. customThe mixture thus obtained
  2. distillationwas distilled under a reduced pressure
  3. customto remove the solvent and thionyl chloride
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f638d328536240daa5dfffc75a950565
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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