Ethyl Acetate → (4-Amino-3'-chloro-biphenyl-3-yl)-dimethyl-methanol

HRID 277838Notes

Reaction equation

HRID 277838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[CH3:18][Mg]Br.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([CH3:18])([CH3:16])[OH:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 159081311-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 15908132(4-Amino-3'-chloro-biphenyl-3-yl)-dimethyl-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (0.55 g, 2.2 mmol) in anhydrous THF under nitrogen was added a solution of methyl magnesium bromide (3.0 M in diethyl ether, 1 mL, 3 mmol) at 0° C. The mixture was slowly warmed to room temperature and kept stirring under nitrogen for 18 hours. The mixture was treated with 10 mL of saturated ammonium chloride aqueous solution and ethyl acetate (50 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (20 mL) and dried (MgSO4). After removal of the solvent, the residue was purified by a flash chromatography (silica gel, hexane:ethyl acetate/2:1) to afford the title compound as an off-white solid: 186-188° C. (HCl salt). Anal. Calc. For C15H17Cl2NO: C, 60.42, H, 5.75, N, 4.7. Found: C, 60.51, H, 5.62, N, 4.56.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×15 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent
  7. customthe residue was purified by a flash chromatography (silica gel, hexane:ethyl acetate/2:1)

Sources & evidence

ORD record
ord-cadd94a21b624d5fa14624d00fb426f0
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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