Ammonium Chloride → HCID 10753521, compound

HRID 928882Notes

Reaction equation

HRID 928882 reaction equation
[CH:1](=[N:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Cl)([CH3:19])[CH3:18].[NH4+].[Cl-]>C1COCC1>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compoundHCID 178489586HCID 178489586, compound

Product 1

HCID 10753521HCID 10753521, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To (E)-N-benzylidene-2-methoxyaniline (5.00 g, 23.7 mmol, 1.00 equiv) in anhydrous THF (106 mL) at 0° C. was added isopropylmagnesium chloride (13.0 mL, 2.0 M in Et2O, 26.0 mmol, 1.10 equiv) and the reaction mixture was stirred at 0° C. for 1 h. A saturated aqueous solution of NH4Cl (50 mL) was added and the aqueous layer was extracted with Et2O (3×50 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on SiO2, eluting with 2% v/v EtOAc/hexanes, to give 2-methoxy-N-(2-methyl-1-phenylpropyl)aniline as a colorless oil (1.72 g, 28% yield).

Workup

  1. extractionthe aqueous layer was extracted with Et2O (3×50 mL)
  2. washThe combined organic layers were washed with brine (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2
  7. washeluting with 2% v/v EtOAc/hexanes

Sources & evidence

ORD record
ord-21074e248a9a4599aa5a851c4db99829
Source dataset
uspto-grants-2016_03
Patent number
US09290591B2

Reaction notes

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