Sodium Chloride → 4-AMino-benzenepropanaMide

HRID 1190091Notes

Reaction equation

HRID 1190091 reaction equation
S(=O)(=O)(O)O.C[O:7][C:8](=O)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.[Na+].[Cl-].[NH4+:21].[OH-]>O.[Cl-].[Na+].O>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:8]([NH2:21])=[O:7])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 68945666HCID 68945666, compound

Product 1

HCID 135960744-AMino-benzenepropanaMideYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 3-(4-amino-phenyl)-propionic acid methyl ester sulfuric acid salt (as prepared in the previous step, 277 mg, 1.00 mmol) in 8 mL of conc NH4OH was added 0.75 g of NaCl in 3 mL of H2O. After stirring at RT for 16 h, the resulting mixture was treated with 10 mL of brine and extracted with EtOAc (5×25 mL). The combined organic layers were dried (Na2SO4) and concentrated to give 133 mg (81%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C9H12N2O, 165.1 (M+H). found 165.0.

Workup

  1. extractionextracted with EtOAc (5×25 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-559ac170e46941c9acc5e62d5b3fb1aa
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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