Dimethyl acetylenedicarboxylate → HCID 178418266, compound

HRID 3115

Reaction equation

HRID 3115 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:3]=1[C:4]([O:6]C)=O.[C:14]([C:20]([O:22][CH3:23])=[O:21])#[C:15][C:16]([O:18][CH3:19])=[O:17].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[O:12][CH3:13])[N:1]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:14]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 12318577Methyl 2-amino-6-methoxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 178418266HCID 178418266, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of methyl 2-amino-6-methoxybenzoate ((1.30 g, 7.17 mM) and dimethyl acetylenedicarboxylate (1.17 g, 8.23 mM) in t-butanol (11 mL) was refluxed under a nitrogen atmosphere for 4 hr. The reaction mixture was cooled to room temperature, potassium t-butoxide (0.92 g, 8.23 mM) was added, and the resulting mixture was heated to 90° C. for 1.5 hr during which solids precipitated out of solution. The mixture was cooled to room temperature, filtered and the collected solids were dissolved in water. The resulting solution was acidified with 1N H2SO4 to form a light tan precipitate. The solids were collected, filtered, washed with water and air dried to provide the desired compound (1.35 g, 65%) as a tan solid. A 0.28 g portion of this material was recrystallized from ethyl acetate to provide an analytical sample (0.24 g) of the title compound as a white solid, mp 184°-186° C.; MS(CI): 292 (M+H).

Workup

  1. temperaturethe resulting mixture was heated to 90° C. for 1.5 hr during which solids
  2. customprecipitated out of solution
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered
  5. dissolutionthe collected solids were dissolved in water
  6. customto form a light tan precipitate
  7. customThe solids were collected
  8. filtrationfiltered
  9. washwashed with water and air
  10. customdried

Sources & evidence

ORD record
ord-1239a307ee3d4a5296ffa6fb6b34bcfc
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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