4-Aminobenzoic Acid → 4-amino-N-(pyridin-3-ylmethyl)benzamide

HRID 1011240Notes

Reaction equation

HRID 1011240 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][NH2:18])[CH:12]=1.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:18][CH2:17][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 178418300HCID 178418300, compound

Product 1

HCID 5778334-amino-N-(pyridin-3-ylmethyl)benzamideYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottom flask a suspension of 4-amino-benzoic acid (2 g, 14.58 mmol), C-pyridin-3-yl-methylamine (1.48 mL, 14.58 mmol), hydroxybenzotriazole (HOBt, 2.17 g, 16.04 mmol) and triethylamine (4.06 mL, 29.16 mmol) in dichloromethane (150 mL) is cooled to 0° C. and EDCI*HCl (3.08 g, 16.04 mmol) is added. The reaction mixture is stirred at room temperature for 20 hours. The solvent is removed in vacuo and ice cooled water is added. The precipitate is collected by filtration, washed once with 1 N NaOH, three times with water, two times with petroleum ether and dried in vacuo to give the title compound (2.56 g) as a solid.

Workup

  1. customThe solvent is removed in vacuo and ice
  2. temperaturecooled water
  3. additionis added
  4. filtrationThe precipitate is collected by filtration
  5. washwashed once with 1 N NaOH, three times with water, two times with petroleum ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-326221c086b04215bdffcf71c90d7c27
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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