Acetic Acid → Methyl 2-(benzylamino)-4-fluorobenzoate

HRID 1045142

Reaction equation

HRID 1045142 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:13]([NH:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 14075433Methyl 2-amino-4-fluorobenzoate

Product 1

HCID 43735197Methyl 2-(benzylamino)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-amino-4-fluorobenzoate (0.90 g), benzaldehyde (0.54 mL), sodium triacetoxyborohydride (1.58 g) and acetic acid (0.3 mL) in CH2Cl2 (20 mL) were stirred for 3 hours. The reaction was quenched with methanol, concentrated, and chromatographed on silica gel with 5% ethyl acetate/hexanes.

Workup

  1. customThe reaction was quenched with methanol
  2. concentrationconcentrated
  3. customchromatographed on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e40a7db9b9394ec0a2ac589f2b56a313
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Linked notes

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