Water → 2-Amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid

HRID 591841Notes

Reaction equation

HRID 591841 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[NH2:17].[OH-].[Li+].O>C1COCC1.CO>[NH2:17][C:5]1[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][C:4]=1[C:3]([OH:18])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 666709102-Amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester

Product 1

HCID 666708712-Amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester (1.04 g, 4.19 mmol) in a mixture of THF (8 mL) and methanol (5 mL) was added lithium hydroxide (0.36 g), followed by water (3 mL). The reaction mixture was stirred at room temperature overnight, and then refluxed for 4 hours. After cooling to room temperature, the was solvent concentrated. The pH was adjusted to approximately 5 with 2 N aqueous hydrochloric acid and the residue was evaporated to dryness to give 2-amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid as a chloride salt. Yield: 1.84 g. The crude material was used in the next step without further purification.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationthe was solvent concentrated
  4. customthe residue was evaporated to dryness

Sources & evidence

ORD record
ord-d56e0286753c4cd298a7022206f1f422
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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