Acetic Acid → 4-(benzylamino)benzoic acid

HRID 2380966Notes

Reaction equation

HRID 2380966 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.O>[CH2:11]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 9784-Aminobenzoic AcidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 8535464-(benzylamino)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-aminobenzoic acid (10 g, 73 mmol) in tetrahydrofuran (200 ml) was added benzaldehyde (9.63 ml, 95 mmol), acetic acid (4.9 ml, 91.3 mmol) followed by sodium triacetoxyborohydride (31 g, 146 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (200 ml) and extracted with dichloromethane (2×200 ml). The organics were combined, washed with brine, dried over magnesium sulfate and then concentrated in vacuo. The residue was purified by flash chromatography (SiO2) eluting with diethylether/dichloromethane (1:4) to afford the title compound as an off white solid (4.74 g, 28% yield). HPLC retention time 5.32 min. Mass spectrum (ES+) m/z 228 (M+H).

Workup

  1. extractionextracted with dichloromethane (2×200 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2)
  6. washeluting with diethylether/dichloromethane (1:4)

Sources & evidence

ORD record
ord-0d5ad285d3ca4325991df50f30e4b796
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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