Methyl 4-aminobenzoate → HCID 670109, compound

HRID 642122Notes

Reaction equation

HRID 642122 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.[C:12](Cl)(=[O:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH2:14][CH2:13][C:12]([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:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 64801Benzenepropanoyl chloride

Product 1

HCID 670109HCID 670109, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 4-aminobenzoate (825 mg, 5.46 mmol) in anydrous pyridine (16 mL) was added dropwise hydrocinnamoyl chloride (990 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, 1200 mg) was added and the resulting mixture was stirred overnight at rt. After rinsing the resin and filtration, water (200 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 (1.40 g) was obtained as a white solid (90%) in 98.2% 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, 1200 mg) was added
  2. washAfter rinsing
  3. filtrationthe resin and filtration, water (200 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-5bb1d7d8561547e0b89fe47609994906
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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