Ethyl 2-aminobenzoate → HCID 21906964, compound

HRID 1246964Notes

Reaction equation

HRID 1246964 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.[BH3-]C#N.[Na+]>CO>[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 133894-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21906964HCID 21906964, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-aminobenzoate (4 g) and 4-pyridylformaldehyde (1.2 eq) and NaBH3CN (2 eq) in methanol stirred overnight. The solvent was evaporated, and EtOAc (100 ml) and H2O (100 ml) were added. The solution was extracted three times with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to give ethyl 2-[(4-pyridylmethyl)-amino]benzoate. The above compound (400 mg) was stirred with acetyl chloride (1.2 eq) and DIEA (1.2 eq) in dichloromethane at RT for two hours. The solution was washed with H2O followed by brine, dried over Na2SO4 and evaporated to give ethyl 2-[N-(4-pyridyl-methyl)acetylamino]benzoate for next step without further purification.

Workup

  1. customThe solvent was evaporated
  2. additionEtOAc (100 ml) and H2O (100 ml) were added
  3. extractionThe solution was extracted three times with EtOAc
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bda2979eab054ac6b2a596c0f1b173d8
Source dataset
uspto-grants-2006_10
Patent number
US07129252B2

Reaction notes

Loading…