Acetic Acid → Methyl 3-[(2-fluoroanilino)methyl]benzoate

HRID 1754315Notes

Reaction equation

HRID 1754315 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][CH:18]=[CH:17][C:15]=1[NH2:16].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][CH:18]=[CH:17][C:15]=1[NH:16][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 95842-FluoroanilineHCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86720274Methyl 3-[(2-fluoroanilino)methyl]benzoateYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 3-formylbenzoate (1 g, 6.092 mmol) in anhydrous DCM (30 mL) was added 2-fluoroaniline (0.620 mL, 6.396 mmol) followed by glacial acetic acid (0.350 mL, 6.092 mmol). The reaction was stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (3.23 g, 15.23 mmol) was added, and the reaction was stirred at room temperature for 3 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 yellow oil (1.57 g, quantitative yield).

Workup

  1. stirringthe reaction was stirred at room temperature for 3 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-f813ef39248c46d1a314020f7fc22839
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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