Methyl iodide → 1-(4-Acetylamino-5-chloro-2-methoxyphenyl)-5-chloropentan-1-one

HRID 963341

Reaction equation

HRID 963341 reaction equation
[C:1]([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])=[C:7]([OH:19])[CH:6]=1)(=[O:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].IC>C(C(C)=O)C>[C:1]([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])=[C:7]([O:19][CH3:20])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 190818791-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one

Product 1

HCID 190818611-(4-Acetylamino-5-chloro-2-methoxyphenyl)-5-chloropentan-1-oneYield 67.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one (1.07 g, 3.5 mmol), potassium carbonate (1.38 g, 10.0 mmol) and iodomethane (0.62 mL, 10.0 mmol) were combined in methyl ethyl ketone (20 mL) and stirred at reflux temperature for 4 hours, 15 minutes. The mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed in brine, dried over sodium sulfate, and then evaporated to leave a solid residue. Crystallization of the residue from ethyl acetate-hexanes gave 1-(4-acetylamino-5-chloro-2-methoxyphenyl)-5-chloro-pentan-1-one (0.720 g, 2.37 mmol), m.p. 98°-100° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. custom15 minutes
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed in brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto leave a solid residue
  9. customCrystallization of the residue from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-12c40d93e8884fb3b03071ddda14a120
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Linked notes

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