Dimethyl acetylenedicarboxylate → HCID 178418285, compound

HRID 3106

Reaction equation

HRID 3106 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6]C)=O.[C:13]([C:19]([O:21][CH3:22])=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[OH:6][C:4]1[C:3]2[C:2](=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:12])[N:1]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 583916Benzoic acid, 2-amino-6-methyl-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 178418285HCID 178418285, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A stirred mixture of methyl 2-amino-6-methylbenzoate (1.50 g, 9.08 mM) and dimethyl acetylenedicarboxylate (1.40 g, 9.82 mM) in t-butanol (20 mL) was refluxed fpr 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (1.10 g, 9.82 mM) was added in one portion whereupon a precipitate formed. After refluxing this mixture for 1.5 hr, it was cooled to room temperature and filtered to separate the solids. The solids were dissolved in water and the resulting solution acidified with 1N H2SO4 to form a precipitate. The mixture was filtered and the collected solids were washed with water and dried to give the title compound (1.66 g, 66.4%) as a tan solid. An analytical sample of this material was obtained by recrystallization of a portion from ethyl acetate/hexane to give off white crystals, mp 167°-168° C.; MS(CI): 276 (M+H).

Workup

  1. temperaturewas refluxed fpr 18 hr under a nitrogen atmosphere
  2. customformed
  3. temperatureAfter refluxing this mixture for 1.5 hr
  4. temperatureit was cooled to room temperature
  5. filtrationfiltered
  6. customto separate the solids
  7. dissolutionThe solids were dissolved in water
  8. customto form a precipitate
  9. filtrationThe mixture was filtered
  10. washthe collected solids were washed with water
  11. customdried

Sources & evidence

ORD record
ord-3dda300c17224ab9a94f5d53c331760a
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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