HCID 66599889, compound → 5',6'-Diamino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-ol

HRID 1909061Notes

Reaction equation

HRID 1909061 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O>[Pd].CO>[NH2:15][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 66599889HCID 66599889, compound

Product 1

HCID 665998245',6'-Diamino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-olYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a parr flask was added 6′-Amino-5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ol (10.0 g, 42.0 mmol) (Step 1), 10% Pd/C (2.5 g) and MeOH (100 mL). The flask was pressurized to 50 psi with H2 for 12 hr with shaking. The contents of the flask were filtered through Celite and the filtrate (dark green) was concentrated to afford 5′,6′-Diamino-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ol as a dark purple solid (8.90 g, 39.7 mmol, 95%). MS ESI m/z 209.2 (M+H)+.

Workup

  1. filtrationThe contents of the flask were filtered through Celite
  2. concentrationthe filtrate (dark green) was concentrated

Sources & evidence

ORD record
ord-cfa05906e22748519dfcd5b964cff2a1
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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