Hydrazine hydrate (1:1) → HCID 21825590, compound

HRID 917832Notes

Reaction equation

HRID 917832 reaction equation
[N+:1]([C:4]1[N:5]=[N:6][N:7]([C@@H:9]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH:8]=1)([O-])=O.O.NN>CO.[Pd]>[NH2:1][C:4]1[N:5]=[N:6][N:7]([C@@H:9]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21825588HCID 21825588, compound

Product 1

HCID 21825590HCID 21825590, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 16 (1.23 g, 0.005 mol) in methanol (25 ml) and 5% palladium-on-carbon catalyst (250 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. The product was crystallized from ethyl acetate-methanol (3:1) to give 1.0 g (92%) of 18, m.p. 102°-104°. The nmr spectrum indicated the presence of ethyl acetate. After heating at 100° in vacuo overnight 18 had a melting point of 141°-143°: [α]D25 -65.8° (c 1.00, water); nmr (DMSO-d6) δ 5.77 (d, 1, J1',2' 4.0 Hz, 1'--H), 7.34 (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
  4. customThe product was crystallized from ethyl acetate-methanol (3:1)

Sources & evidence

ORD record
ord-80ac10f02ff64fedb32443da65dff749
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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