3-(2-aminoethyl)benzoic acid → Benzoic Acid

HRID 2051606Notes

Reaction equation

HRID 2051606 reaction equation
NCC[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].C([O-])(=O)C.[Na+].C(N1C=CC=C(C(Cl)=O)C1=O)C1C=CC=CC=1>CC(C)=O>[C:7]([OH:9])(=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 5060773-(2-aminoethyl)benzoic acidHCID 517045Sodium AcetateHCID 54192812HCID 54192812, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20 ml of acetone are added to 16 ml of an about 1 molar solution of 3-(2-aminoethyl)-benzoic acid containing the corresponding amount of sodium acetate, and 3.7 g of 1-benzyl-1,2-dihydro-2-oxo-nicotinic acid chloride (prepared from 1-benzyl-1,2-dihydro-2-oxo-nicotinic acid and thionyl chloride) are added with agitation and cooling. Agitation is then continued for 1 hour at room temperature, the acetone is removed under reduced pressure, and dilute hydrochloric acid is added to the residue. The precipitated product is suction-filtered, reprecipitated from dilute ammonia, and recrystallized from dilute methanol. The 4-(2-<1-benzyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzoic acid so obtained has a melting point of 150°-152° C. and of 171°-173° C.

Workup

  1. additionare added with agitation
  2. temperaturecooling
  3. customthe acetone is removed under reduced pressure, and dilute hydrochloric acid
  4. additionis added to the residue
  5. filtrationThe precipitated product is suction-filtered
  6. customreprecipitated from dilute ammonia
  7. customrecrystallized from dilute methanol

Sources & evidence

ORD record
ord-e09a6bed016e41418d602499804ea3f8
Source dataset
uspto-grants-1980_01
Patent number
US04181658

Reaction notes

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