4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid → 3-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid

HRID 74158

Reaktionsgleichung

Reaktionsgleichung von HRID 74158
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[N+:17]([O-])=O)[CH2:3][CH2:2]1>C1COCC1.CO.[Pd]>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 1

HCID 436103324-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid

Produkt 1

HCID 548880483-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acidAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid (see Working Example 4-1) (202 g, 0.76 mol) was dissolved in a solvent mixture of THF (2.2 L) and methanol (1.5 L), Pd/C (5%, wet, 20 g) was added, and hydrogenation was carried out under 5 atm. Hydrogen absorption stopped at 3 h, and after the system was purged with argon the catalyst was removed by filtration, and the filtrate was concentrated at reduced pressure to yield the title compound (180 g, quant.) as a dark gray solid.

Aufarbeitung

  1. additionwas added
  2. customHydrogen absorption
  3. customafter the system was purged with argon the catalyst
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b340ee561d764d2ea478af19f7930b3d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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