3-Nitrophthalic acid → 3-Aminophthalic acid

HRID 55749

반응식

HRID 55749 반응식
[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]

참가 물질

5

반응물 2

HCID 690433-Nitrophthalic acidHCID 178418361HCID 178418361, 화합물3회

생성물 1

HCID 794903-Aminophthalic acid수율 84%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aac163278d774f779aaceb5fc6c049d3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433606B2

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