Potassium Iodide → Methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate

HRID 1608059Notes

Reaction equation

HRID 1608059 reaction equation
[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([OH:20])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([O:31][CH3:32])=[O:30].[I-].[K+]>CN(C)C=O>[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([O:20][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 140149555-Benzoylamino-1-hydroxy-5,6,7,8-tetrahydro-naphthalene

Product 1

HCID 14014967Methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

50 mmol of 5-benzoylamino-1-hyroxy-5,6,7,8-tetrahydro-naphthalene and 100 ml of anhydrous potassium potassium carbonate are stirred at 50° C. in 100 ml of absolute dimethylformamide for 20 minutes. A solution of 60 mmol of methyl chloroacetate and 25 mmol of potassium iodide in 25 ml dimethylformamide is added dropwise and the mixture is stirred at 50° C. for 6 to 8 hours. It is filtered under the influence of heat, the residue is rinsed thoroughly with ethyl acetate and the filtrate is evaporated. The residue is stirred in a mixture of 10% strength NaOH and ethyl acetate or tetrahydrofuran for 10 minutes. The ethyl acetate phase is extracted by shaking once with 10% strength NaOH, dried over Na2SO4 and evaporated. The residue is recrystallized from ethyl acetate.

Workup

  1. filtrationIt is filtered under the influence
  2. temperatureof heat
  3. washthe residue is rinsed thoroughly with ethyl acetate
  4. customthe filtrate is evaporated
  5. stirringThe residue is stirred in a mixture of 10% strength NaOH and ethyl acetate or tetrahydrofuran for 10 minutes
  6. extractionThe ethyl acetate phase is extracted
  7. stirringby shaking once with 10% strength NaOH
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b9c0ab04ff9e49c9b482ca914fd769d5
Source dataset
uspto-grants-1989_09
Patent number
US04868331

Reaction notes

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