Dimethyl acetylenedicarboxylate → HCID 178418266、化合物

HRID 3115

反応式

HRID 3115 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 178418266HCID 178418266、化合物収率 65%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1239a307ee3d4a5296ffa6fb6b34bcfc
出典データセット
uspto-grants-1998_03
特許番号
US05733910

関連ノート

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