Hydrochloric Acid → HCID 54289209, compound

HRID 542940Notes

Reaction equation

HRID 542940 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:17][CH3:18])[C:11]=1[N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[C:6]([OH:8])=[O:7].Cl.[CH3:20]O>>[CH3:20][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([O:17][CH3:18])[C:11]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21280956HCID 21280956, compound

Product 1

HCID 54289209HCID 54289209, compound

Procedure

A suspension of 35.8 g. of 3,5-dimethoxy-4-(N-methyl-acetamido)-benzoic acid in 500 ml. of absolute methanol was saturated with dry hydrogen chloride, whereby a solution gradually formed. After standing at room temperature for 20 hours, the solution was evaporated to dryness under vacuum. The residue was treated with 200 ml. of ice-water and with a concentrated sodium hydroxide solution until a strongly alkaline reaction was achieved and the resulting emulsion was extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extracts were washed with two 100 ml. portions of water, combined, dried over magnesium sulfate, filtered and evaporated under vacuum. After recrystallization from ethyl acetate/cyclohexane, the residue yielded 3,5-dimethoxy-4-(N-methylacetamido)-benzoic acid methyl ester having a melting point of 115°-116° C.

Workup

  1. additionA suspension of 35.8 g
  2. customgradually formed
  3. customthe solution was evaporated to dryness under vacuum
  4. additionThe residue was treated with 200 ml
  5. customof ice-water and with a concentrated sodium hydroxide solution until a strongly alkaline reaction
  6. extractionthe resulting emulsion was extracted with two 500 ml
  7. washThe ethyl acetate extracts were washed with two 100 ml
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customAfter recrystallization from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-04c7411e29724b2198a0195eee7bd13d
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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