Potassium Hydroxide → Ethyl N-[2-(3-chloro-4-hydroxyphenyl)-1-methyl-2-oxoethyl]carbamate

HRID 1198900Notes

Reaction equation

HRID 1198900 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([C:16](=[O:25])[CH:17]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH3:18])[CH:7]=[CH:8][C:9]=1[O:10]C(OCC)=O>O.CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:16](=[O:25])[CH:17]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH3:18])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 14370690ethyl N-[2-(3-chloro-4-ethoxycarbonyloxyphenyl)-1-methyl-2-oxoethyl]carbamate

Product 1

HCID 14370691Ethyl N-[2-(3-chloro-4-hydroxyphenyl)-1-methyl-2-oxoethyl]carbamateYield 71.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 12.50 g of 85% potassium hydroxide (i.e. potassium hydroxide of purity about 85%, of which the main impurity is water) dissolved in a mixture of 20 ml of water and 30 ml of methanol was added dropwise, whilst ice-cooling, to a solution of 10.87 g of ethyl N-[2-(3-chloro-4-ethoxycarbonyloxyphenyl)-1-methyl-2-oxoethyl]carbamate [prepared as described in step (a) above] in 130 ml of methanol over a period of 5 minutes. The mixture was then stireed at room temperature for 20 minutes. At the end of this time, the mixture was concentrated by evaporation under reduced pressure and then acidified with 5% w/v aqueous hydrochloric acid. It was then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried. The ethyl acetate of the solvent was then removed by evaporation under reduced pressure. The residue was recrystallized from a mixure of ethyl acetate and hexane, to give 6.12 g of the title compound as a yellowish-brown powder melting at 106°-108° C.

Workup

  1. additionwas added dropwise, whilst ice-
  2. concentrationAt the end of this time, the mixture was concentrated by evaporation under reduced pressure
  3. extractionIt was then extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. customThe ethyl acetate of the solvent was then removed by evaporation under reduced pressure
  7. customThe residue was recrystallized from a mixure of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f69535af29224b64a88dd2c991b8f614
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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