Methyl 4-aminobenzoate → Methyl 4-[(4-heptylbenzoyl)amino]benzoate

HRID 642074Notes

Reaction equation

HRID 642074 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>N1C=CC=CC=1>[CH2:12]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[O:24])=[CH:26][CH:27]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 170864Benzoyl chloride, 4-heptyl-

Product 1

HCID 68409708Methyl 4-[(4-heptylbenzoyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anhydrous pyridine (10 mL) was added dropwise 4-heptylbenzoyl chloride (950 μL) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (125 mL) was added to the filtrate and a white solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. overnight. The title compound (1051 mg) was obtained as a white solid (90%) in 96.9% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionAfter 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (125 mL)
  4. additionwas added to the filtrate
  5. filtrationFiltration
  6. washwashing with water
  7. customgave a solid which
  8. customwas dried under vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-b81589544adf4688818c797e2f5c5931
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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