Methyl 4-Formylbenzoate → HCID 28738322, compound

HRID 1256938Notes

Reaction equation

HRID 1256938 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1)=[O:4].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 15294Methyl 4-FormylbenzoateHCID 660364-ChlorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate water

Product 1

HCID 28738322HCID 28738322, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-formyl benzoic acid methyl (10.0 g) in chloroform (300 ml), 4-chlorobenzylamine (11.2 g) was added, and the mixed solution was stirred for 15 min. Then, to the resulting solution, sodium triacetoxyborohydride (16.8 g) was added, and the mixed solution was stirred at room temperature for two hours. To the resulting solution, acetic acid (10.5 ml) was added, and the solution was stirred for four hours. Saturated sodium bicarbonate water was added, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to remove the solvent, and the resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=15 to 50%) to give methyl 4-{[(4-chlorobenzyl)amino]methyl}benzoate (13.8 g).

Workup

  1. stirringthe mixed solution was stirred at room temperature for two hours
  2. stirringthe solution was stirred for four hours
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customthe resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=15 to 50%)

Sources & evidence

ORD record
ord-927f1c63ceab4589be3a3b789254141d
Source dataset
uspto-grants-2013_06
Patent number
US08461329B2

Reaction notes

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