Acetic Acid → Methyl 3-(((4-fluorophenyl)amino)methyl)benzoate

HRID 1497974Notes

Reaction equation

HRID 1497974 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][CH2:1][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86720703Methyl 3-(((4-fluorophenyl)amino)methyl)benzoateYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 3-formylbenzoate (0.5 g, 3.046 mmol) in anhydrous DCM (15 mL) was added 4-fluoroaniline (0.303 mL, 3.198 mmol) followed by glacial acetic acid (0.174 mL, 3.046 mmol). The reaction was stirred at room temperature for 64 hours. Sodium triacetoxyborohydride (1.614 g, 7.615 mmol) was added, and the reaction was stirred at room temperature for 2 hours. Water was added to quench the reaction and the mixture was diluted with DCM. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound as a red oil (0.805 g, quantitative yield).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. customto quench
  3. customthe reaction
  4. washThe organic layer was washed with brine
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cc69621a138541c098de318bb7fd0dc2
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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