4-(Aminomethyl)Benzoic Acid → HCID 9817339, compound

HRID 430024Notes

Reaction equation

HRID 430024 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]([O:11]C)=O)[CH:2]=1.[NH2:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.C1CCN2C(=NCCC2)CC1>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=2)=[O:11])[CH:2]=1

Participants

5

Reactant 3

HCID 655264-(Aminomethyl)Benzoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23008475Methyl 2-(pyridin-3-yloxy)acetate

Product 1

HCID 9817339HCID 9817339, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

32 g (0.19 mole) of methyl 2-(pyridin-3-yloxy)-acetate, 27 g (0.18 mole) of 4-aminomethylbezoic acid and 59 g (0.39 mole) of DBU were added to ethanol (350 ml), and reaction was then carried out at room temperature for 24 hours. After the reaction mixture had been concentrated, partition was carried out between toluene and water. Concentrated hydrochloric acid was added to the resultant aqueous layer to accomplish neutralization, and a deposited solid was collected by filtration, washed with water and methanol, and then dried to obtain 46 g (yield: 89%) of 4-[N-(pyridin-3-yl)oxyacetylaminomethyl]benzoic acid.

Workup

  1. concentrationAfter the reaction mixture had been concentrated
  2. custompartition
  3. additionConcentrated hydrochloric acid was added to the resultant aqueous layer
  4. filtrationa deposited solid was collected by filtration
  5. washwashed with water and methanol
  6. customdried

Sources & evidence

ORD record
ord-15504926cf1f45c183b062b3a160bb04
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

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