D-Psicose → 4-N-cyclopropylpyridine-3,4-diamine

HRID 2170987Notes

Reaction equation

HRID 2170987 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N+:11]([O-])=O)[CH2:3][CH2:2]1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.[Pd]>[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[NH2:11])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 22349359N-Cyclopropyl-3-nitropyridin-4-amine

Product 1

HCID 191025534-N-cyclopropylpyridine-3,4-diamineYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the intermediate 5-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20° C. with wet 10% Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with MTBE to afford compound 5-c as a yellow powder (133 g, 95%).

Workup

  1. customat 20° C.
  2. customovernight
  3. filtrationAfter uptake of H2 (3 eq.), the catalyst was filtered off
  4. customthe filtrate was evaporated
  5. washThe residue was washed with MTBE

Sources & evidence

ORD record
ord-dfda28383b9a4d6f98dffe35e8a6b865
Source dataset
uspto-grants-2015_06
Patent number
US09051317B2

Reaction notes

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