3-Nitrophthalic acid → 3-Aminophthalic acid

HRID 55749

反応式

HRID 55749 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14]

参加物

5

反応物 2

HCID 690433-Nitrophthalic acidHCID 178418361HCID 178418361、化合物3 回

生成物 1

HCID 794903-Aminophthalic acid収率 84%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

10% Pd/C (2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator under a nitrogen atmosphere. Hydrogen was charged to the reaction vessel for up to 55 psi. The mixture was shaken for 13 hours, maintaining hydrogen pressure between 50 and 55 psi. Hydrogen was released and the mixture was purged with nitrogen 3 times. The suspension was filtered through a celite bed and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solid was reslurried in ether and isolated by vacuum filtration. The solid was dried in vacuo to a constant weight, affording 54 g (84% yield) of 3-aminophthalic acid as a yellow product. 1H-NMR (DMSO-d6) δ: 3.17 (s, 2H), 6.67 (d, 1H), 6.82 (d, 1H), 7.17 (t, 1H), 8-10 (br, s, 2H); 13C-NMR (DMSO-d6) δ: 112.00, 115.32, 118.20, 131.28, 135.86, 148.82, 169.15, 170.09.

後処理

  1. customthe mixture was purged with nitrogen 3 times
  2. filtrationThe suspension was filtered through a celite bed
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customisolated by vacuum filtration
  6. customThe solid was dried in vacuo to a constant weight

出典と根拠

ORDレコード
ord-aac163278d774f779aaceb5fc6c049d3
出典データセット
uspto-grants-2016_09
特許番号
US09433606B2

関連ノート

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