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

HRID 74158

Reaction equation

HRID 74158 reaction equation
[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]

Participants

5

Reactant 1

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

Product 1

HCID 548880483-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acidYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b340ee561d764d2ea478af19f7930b3d
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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