4-Aminobenzoic Acid → 4-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)benzoic acid

HRID 1494621

反応式

HRID 1494621 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CC(N(C)C)=O.C1(C)C=CC=CC=1.[CH:24]12[CH2:30][CH:27]([CH:28]=[CH:29]1)[CH:26]1[C:31]([O:33][C:34](=O)[CH:25]21)=[O:32]>O>[O:32]=[C:31]1[CH:26]2[CH:25]([CH:24]3[CH2:30][CH:27]2[CH:28]=[CH:29]3)[C:34](=[O:33])[N:1]1[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 9784-Aminobenzoic AcidHCID 1140TolueneHCID 13223826-62-0HCID 31374Dimethylacetamide

生成物 1

HCID 5486924-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)benzoic acid収率 94.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
165 °C

実験手順

To 4-aminobenzoic acid (800 g, 5.83 mol) is added dimethylacetamide (2.5 l), toluene (1 l), and slowly with stirring bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (956 g, 5.83 mol). After the addition the mixture is stirred for 1 hour, raised to 140° C. with removal of water (100 ml) azeotropically and then raised to 165° C. to remove the toluene. The mixture is cooled and the product precipitated into water (3 l). Filtration, washing with water, drying in an oven at 80° C. and recrystallisation from ethanol yields a white crystalline solid (1.56 kg, 94%). M.p.: 224°-228° C.

後処理

  1. additionAfter the addition the mixture
  2. customto remove the toluene
  3. temperatureThe mixture is cooled
  4. customthe product precipitated into water (3 l)
  5. filtrationFiltration
  6. washwashing with water
  7. customdrying in an oven at 80° C.
  8. customrecrystallisation from ethanol

出典と根拠

ORDレコード
ord-d3a8efd0c8b9494ebc1bfc8142b95f30
出典データセット
uspto-grants-1991_06
特許番号
US05026871

関連ノート

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