Acetic Acid → Benzoic acid, 2-[(4-pyridinylmethyl)amino]-, methyl ester

HRID 891263Notes

Reaction equation

HRID 891263 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[C:13]([O:22][CH3:23])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH2:16].C([BH3-])#N.[Na+]>CO>[N:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:16][C:15]2[C:14](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([O:22][CH3:23])=[O:21])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8635Methyl AnthranilateHCID 133894-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 10879301Benzoic acid, 2-[(4-pyridinylmethyl)amino]-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 mL Acetic acid and 8.6 g 4-pyridinecarbaldehyde are added to a solution of 7.5 g methyl anthranilate in 300 mL methanol. The mixture is stirred for 12 hours under nitrogen atmosphere at room temperature. 5.7 g Sodium cyanotrihydridoborate (85%) is added and the mixture is stirred for 3 hours at room temperature. Additional 1.14 g sodium cyanotrihydridoborate (85%) is added and the mixture is stirred for 12 hours at room temperature. The solvent is evaporated and the residue dissolved in ethyl acetate and washed with saturated NaHCO3 solution and saturated sodium chloride solution. The organic extract is concentrated and purified with hexane/ethyl acetate (1:1) on silica gel to yield methyl N-(4-pyridylmethyl)-anthranilate with m.p. 86° C.

Workup

  1. stirringthe mixture is stirred for 3 hours at room temperature
  2. stirringthe mixture is stirred for 12 hours at room temperature
  3. customThe solvent is evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with saturated NaHCO3 solution and saturated sodium chloride solution
  6. extractionThe organic extract
  7. concentrationis concentrated
  8. custompurified with hexane/ethyl acetate (1:1) on silica gel

Sources & evidence

ORD record
ord-5179a70e82af4e4eb9a563e0357d2241
Source dataset
uspto-grants-2006_02
Patent number
US07002022B2

Reaction notes

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