Sodium borohydride → 4-Methyl-N-(3,4,5-trimethoxybenzyl)aniline

HRID 1647298Notes

Reaction equation

HRID 1647298 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([N:6]=[CH:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15657369HCID 15657369, compound

Product 1

HCID 3737984-Methyl-N-(3,4,5-trimethoxybenzyl)anilineYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (108a) (6.0 g, 21.1 mmol) in ethanol (100 mL) was added NaBH4 (4.06 g, 98%, 105 mmol) in portions. The reaction mixture was stirred at reflux under argon for 2 h. The solvent was removed under reduced pressure. Saturated aqueous NaCl (30 mL) was added to the residue and the mixture extracted with ether (100, 40 and 40 mL). The combined ether layer was washed with saturated NaCl solution (30 mL), and dried over anhydrous Na2SO4. Evaporation of the filtrate gave 109a (5.6 g, 92.7%) as white crystals: mp 94°-6° C. after recrystallization from ethanol. 1H NMR (200 MHz, CDCl3) δ7.00 (d, J=8 Hz, 2H), 6.61 (s, 2H), 6.58 (d, J=8 Hz, 2H), 4.23 (s, 2H), 3.84 (s, 9H), 2.24 (s, 3H). CIMS (isobutane) m/e 288 (MH+ 76).

Workup

  1. temperatureat reflux under argon for 2 h
  2. customThe solvent was removed under reduced pressure
  3. additionSaturated aqueous NaCl (30 mL) was added to the residue
  4. extractionthe mixture extracted with ether (100, 40 and 40 mL)
  5. washThe combined ether layer was washed with saturated NaCl solution (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-00b02b29e7834ed7813aebd15e57f2c9
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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