Hydrazine hydrate (1:1) → HCID 21825589, compound

HRID 917831Notes

Reaction equation

HRID 917831 reaction equation
[N+:1]([C:4]1[CH:8]=[N:7][N:6]([C@@H:9]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[N:5]=1)([O-])=O.O.NN>CO.[Pd]>[NH2:1][C:4]1[CH:8]=[N:7][N:6]([C@@H:9]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[N:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21825587HCID 21825587, compound

Product 1

HCID 21825589HCID 21825589, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 15 (2.46 g, 0.01 mol) in methanol (50 ml) and 5% palladium-on-carbon catalyst (500 mg) was stirred at room temperature while a solution of 99% hydrazine hydrate in methanol (1:3, v/v) was added dropwise until evolution of nitrogen ceased. The catalyst was removed by filtration through Celite and the solvent was removed by evaporation in vacuo to give 2.30 g of syrup. The syrup was dissolved in methanol and absorbed on 5 g of silica gel. The methanol was removed and the mixture was added to a dry packed silica gel column (2.5 × 28 cm). The column was eluted with chloroform (0.2 liter), chloroform-ethyl acetate (1:1, 0.2 liter), ethyl acetate (0.2 liter), and ethyl acetate-methanol (9:1, 0.5 liter); 20 ml fractions were collected. Fractions 30-35 provided 2.0 g (93%) of 17 as a syrup: nmr (DMSO-d6) δ 5.62 (d, 1, J1',2' 4.0 Hz, 1'--H), 7.03 (s, 1, 5--H).

Workup

  1. additionv/v) was added dropwise until evolution of nitrogen
  2. customThe catalyst was removed by filtration through Celite
  3. customthe solvent was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-1adfca10031b42fba0968a8add6c0cb7
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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