2-(2-(Tert-butoxycarbonyl)hydrazino)-5-nitropyridine → 2-BOC-hydrazino-5-amino pyridine

HRID 37449Notes

Reaction equation

HRID 37449 reaction equation
[C:1]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>[Pd].C(O)C>[C:1]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 103325202-(2-(Tert-butoxycarbonyl)hydrazino)-5-nitropyridine

Product 1

HCID 103763392-BOC-hydrazino-5-amino pyridineYield 81.64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a Parr hydrogenation bottle was added 2-BOC-hydrazino-5-nitropyridine (1 equivalent), 1(7% palladium on charcoal (0.3 gm Pd/gm of pyridine) and ethanol (100 ml/gm of pyridine). The reaction was hydrogenated at 50 psi H2 for 2 hours at room temperature on a Parr hydrogenator. The reaction mixture was filtered through a filter cell plug and rinsed with ethanol. The yellow green solution was concentrated under reduced pressure to give a pale yellow solid. The product was recrystallized from ethanol; yield 81.64%; m.p. 140°-142°. IR (KBr): 3360, 3200, 2980, 1650, 1635, 1580, 1490, 1390, 1360, 1300, 1260, 1160, 1020, 880, 860, 830, 750, 590, 530 cm-1.

Workup

  1. filtrationThe reaction mixture was filtered through a filter cell plug
  2. washrinsed with ethanol
  3. concentrationThe yellow green solution was concentrated under reduced pressure
  4. customto give a pale yellow solid
  5. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-537bb5f492aa4a38a7205c52da5f6114
Source dataset
uspto-grants-1995_05
Patent number
US05420285

Reaction notes

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