Hydrazine hydrate (1:1) → HCID 22046712, compound

HRID 1826140Notes

Reaction equation

HRID 1826140 reaction equation
O.NN.[CH2:4]([O:11][C:12]1[C:26]([O:27][CH3:28])=[CH:25][C:15]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[CH2:23][OH:24])=[O:17])=[C:14]([N+:29]([O-])=O)[C:13]=1[O:32][CH3:33])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H][H]>CO.[Ni]>[NH2:29][C:14]1[C:13]([O:32][CH3:33])=[C:12]([O:11][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:26]([O:27][CH3:28])=[CH:25][C:15]=1[C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][OH:24])=[O:17]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 22046699HCID 22046699, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22046712HCID 22046712, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (2.31 g, 72.2 mmol) was added dropwise to a solution of 125 (6.01 g, 14.4 mmol) in methanol (60 mL) gently refluxing over Raney nickel (1.1 g, slurry). The resulting vigorous evolution of hydrogen gas subsided after approximately 10 minutes and the reaction was deemed to be complete by TLC after 2 h. The reaction mixture was filtered through celite and the solvent evaporated. Distilled water (100 mL) was added to the residue, and the aqueous mixture was extracted with EtOAc (3×100 mL) and the combined organic phase washed with H2O (3×100 mL) and brine (3×100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent afforded the produc as a brown oil (3.97 g, 10.3 mmol, 73%): 1H NMR (270 MHz, CDCl3) δ 1.6-2.2 (m, 4H), 3.5-3.8 (m, 4H), 3.8 (s, 3H), 3.9 (s, 3H), 4.4 (br s, 1H), 5.1 (s, 2H), 6.6 (s, 1H), 7.3-7.6 (m, 5H); 13C NMR (67.8 MHz, CDCl3) δ 171.5, 144.9, 143.5, 141.9, 137.5, 134.6, 128.6, 128.5, 128.3, 128.2, 128.0, 115.1, 107.3, 75.1, 66.9, 61.0, 60.6, 60.4, 56.9, 50.9, 28.5, 24.9, 21.1, 14.2.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent evaporated
  3. additionDistilled water (100 mL) was added to the residue
  4. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  5. washthe combined organic phase washed with H2O (3×100 mL) and brine (3×100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-97b6b90499674175b7741c822106a2dd
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

Loading…