Water → 1-(2-Amino-5-chlorophenyl)-1-phenylethanol

HRID 280513Notes

Reaction equation

HRID 280513 reaction equation
[CH3:1][Mg]Br.[NH2:4][C:5]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].O>CCOCC>[NH2:4][C:5]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:6]=1[C:7]([CH3:1])([OH:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 128702-Amino-5-chlorobenzophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 1029441-(2-Amino-5-chlorophenyl)-1-phenylethanolYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methylmagnesium bromide (267 ml of 3M ether-solution; 0.8 mole) is added during 45 minutes to a solution of 2-amino-5-chlorobenzophenone (46.3 g; 0.2 mole) in 1 liter of ether. The mixture is refluxed for 5 hours and allowed to stand overnight. It is then cooled in ice and decomposed with 400 ml of water. The ether layer is decanted, washed with saturated salt solution dried (MgSO4) and evaporated. The residue is crystallized from ether-Skellysolve B to give 37.1 g (75% yield), mp 93°-94° C., unchanged on recrystallization. Spectral data support the product structure.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureIt is then cooled in ice
  3. customThe ether layer is decanted
  4. washwashed with saturated salt solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue is crystallized from ether-Skellysolve B
  8. customto give 37.1 g (75% yield), mp 93°-94° C.
  9. customunchanged on recrystallization

Sources & evidence

ORD record
ord-5353a71ca11e4ba1ab71e8f9e5ac8188
Source dataset
uspto-grants-1986_05
Patent number
US04590187

Reaction notes

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