Hydrochloric Acid → 1-(4-Amino-5-chloro-2-methoxyphenyl)ethan-1-one

HRID 963359Notes

Reaction equation

HRID 963359 reaction equation
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([NH2:12])=[CH:7][C:6]=1[O:13][CH3:14].C[Li].[CH3:19]COCC.Cl>C1COCC1>[NH2:12][C:8]1[C:9]([Cl:11])=[CH:10][C:5]([C:4](=[O:15])[CH3:19])=[C:6]([O:13][CH3:14])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 190818494-Amino-5-chloro-N,2-dimethoxy-N-methylbenzamideHCID 178418348HCID 178418348, compound

Product 1

HCID 103135481-(4-Amino-5-chloro-2-methoxyphenyl)ethan-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Methoxy-N-methyl-4-amino-5-chloro-2-methoxybenzamide (24.4 g, 100 mmol) was dissolved in THF (400 mL) and the solution was cooled to -400° C. Methyl-lithium in ether (143 mL, 4.4 g, 200 mmol) ) was added and the mixture was allowed to warm to 0° C. Aqueous hydrochloric acid was added and the mixture was extracted into ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and evaporated to leave a solid. Crystallization from ethyl acetate-hexane gave 4'-amino-5'-chloro-2'-methoxyacetophenone (15.0 g, 75 mmol), m.p. 114°-116° C.

Workup

  1. temperaturethe solution was cooled to -400° C
  2. extractionthe mixture was extracted into ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto leave a solid
  7. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5ecaf41dbaff4892bfdd57c6e32c74fc
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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