Methanol → Methyl 5-(aminomethyl)-2-chlorobenzoate

HRID 59325Notes

Reaction equation

HRID 59325 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10].OS(O)(=O)=O.[CH3:19]O>>[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)[C:9]([O:11][CH3:19])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 671163655-(Aminomethyl)-2-chlorobenzoic acid hydrochloride

Product 1

HCID 66524841Methyl 5-(aminomethyl)-2-chlorobenzoate

Procedure

To a solution of 5-(aminomethyl)-2-chlorobenzoic acid hydrochloride (17.0 g, 76.5 mmol) in methanol (200 mL) was added conc. H2SO4 (15 mL). The reaction mixture was refluxed for 15 h. The reaction mixture was concentrated and water was added. The aq. solution was basified with sodium bicarbonate. The reaction mixture was extracted with 10% MeOH:DCM and concentrated to afford 15.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.1 (br s, 2H), 3.73 (s, 2H), 3.85 (s, 3H), 7.50 (s, 2H), 7.77 (s, 1H); MS (m/z): 200.05 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionThe reaction mixture was extracted with 10% MeOH
  5. concentrationDCM and concentrated

Sources & evidence

ORD record
ord-878a1b0cff5840e490275976c176a7b5
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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