Water → HCID 21391824, compound

HRID 461658Notes

Reaction equation

HRID 461658 reaction equation
[ClH:1].[N+:2]([C:5]1[C:6]([NH:11][NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1)([O-])=O.O>C(O)(C)C>[ClH:1].[NH2:2][C:5]1[C:6]([NH:11][NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 21391826HCID 21391826, compound

Product 1

HCID 21391824HCID 21391824, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

The ethyl 3-(3-nitro-2-pyridyl)carbazate hydrochloride 34 g (0.13 mole) was slurried in 300 ml of isopropanol and treated with 4.4 g of 5% pd/C (50% H2O) in 40 ml of isopropanol. The reaction mixture was subjected to hydrogenation at 50 psig. A 24 psig drop at 27°0 was observed (theory 30 No. at 27°), and the mixture was cooled overnight. The crystalline product was collected along with the catalyst. The product was taken up in 300 ml of hot methanol, the catalyst filtered, and the product precipitated from the filtrate, m.p. 217°-219° dec. Yield: 11 g (37%).

Workup

  1. custom(theory 30 No. at 27°)
  2. temperaturethe mixture was cooled overnight
  3. customThe crystalline product was collected along with the catalyst
  4. filtrationthe catalyst filtered
  5. customthe product precipitated from the filtrate, m.p. 217°-219° dec

Sources & evidence

ORD record
ord-b9e86dc768a944dc98e24d7fa3d40d32
Source dataset
uspto-grants-1977_12
Patent number
US04064134

Reaction notes

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