Dimethyl acetylenedicarboxylate → HCID 178418309、化合物

HRID 3102

反応式

HRID 3102 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl: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>[Cl:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]2[C:3]=1[C:4]([OH:6])=[C:13]([C:19]([O:21][CH3:22])=[O:20])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[N:1]2

参加物

5

反応物 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 592849Methyl 2-amino-6-chlorobenzoateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 178418309HCID 178418309、化合物収率 80.4%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A solution of methyl 2-amino-6-chlorobenzoate (3.00 g, 16.2 mM) and dimethyl acetylenedicarboxylate (2.64 g, 18.6 mM) in t-butanol (25 mL) was refluxed under a nitrogen atmosphere for 18 hr. The reaction mixture was cooled to room temperature and potassium t-butoxide (2.09 g, 18.6 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 rarer 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 air dried to give dimethyl 5-chloro-4-hydroxyquinoline-2,3-dicarboxylate (3.84 g, 80.2%) as a tan solid. An 0.25 g portion of this material was recrystallized from ethyl acetate to provide an analytical sample (0.152 g) of the title compound as an off-white solid, mp 174°-176° C.; MS(CI): 296 (M+H). Analysis for C13H10ClNO5.0.01 H2O: Calculated: C, 52.78; H, 3.41; N, 4.73 Found: C, 52.39; H, 3.38; N, 4.67

後処理

  1. customformed
  2. temperatureAfter refluxing this mixture for 1.5 hr
  3. temperatureit was cooled to room temperature
  4. filtrationfiltered
  5. customto separate the solids
  6. dissolutionThe solids were dissolved in rarer and the resulting solution
  7. customto form a precipitate
  8. filtrationThe mixture was filtered
  9. washthe collected solids were washed with water and air
  10. customdried

出典と根拠

ORDレコード
ord-36369dc8420f49d692dad33fc33db94f
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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