Methylamine → 2-Aminomethylbenzoic acid

HRID 1434480Notes

Reaction equation

HRID 1434480 reaction equation
CN.O=C1C2C(=CC=CC=2)C(=O)[N:5]1[CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]>CCO>[NH2:5][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 33132882-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoic acid

Product 1

HCID 2779422-Aminomethylbenzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 40% solution of methylamine (6.14 mL; 7.1 mmol) was added to 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzoic acid C (2 g; 7.1 mmol) and then EtOH (30 mL) was added. After 5 minutes stirring at room temperature the reaction mixture was heated at 50° C. After 2.5 h, the mixture was cooled and the solvent was evaporated under reduced pressure. The crude product was suspended in 50 mL of absolute ethanol and the suspension was stirred at room temperature for 1 h. The solid was filtered and washed with EtOH to afford 2-(aminomethyl)benzoic acid D (0.87 g; 5.8 mmol). Yield 81%.

Workup

  1. temperaturewas heated at 50° C
  2. waitAfter 2.5 h
  3. temperaturethe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. stirringthe suspension was stirred at room temperature for 1 h
  6. filtrationThe solid was filtered
  7. washwashed with EtOH

Sources & evidence

ORD record
ord-d8cb927dd3684227820d558f230b1d1a
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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