Hydrazine hydrate (1:1) → HCID 22046703, compound

HRID 1826135Notes

Reaction equation

HRID 1826135 reaction equation
O.NN.[N+:4]([C:7]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[CH:18][C:8]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17])=[O:10])([O-])=O.[H][H]>CO.[Ni]>[NH2:4][C:7]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[CH:18][C:8]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17])=[O:10]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 22046717HCID 22046717, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22046703HCID 22046703, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (1.33 mL, 41.5 mmol) was added dropwise to a solution of 116 (2.83 g, 8.3 mmol) in methanol (142 mL) gently refluxing over Raney nickel (500 mg, 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 product (2.18 g, 6.5 mmol) as a brown oil: 1H NMR (270 MHz, CDCl3) δ 1.6-2.0 (m, 3H), 2.1-2.2 (m, 1H), 3.4-3.7 (m, 4H), 3.8 (s, 3H), 3.8-3.9 (2×s, 6H), 4.4 (br s, 1H), 4.7-4.3 (br s, 1H), 6.6 (s, 1H); 13C NMR (67.8 MHz, CDCl3) δ 144.7, 144.5, 141.6, 134.6, 107.1, 66.9, 61.0, 60.9, 60.5, 56.8, 50.9, 28.6, 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-20d7396bc81e4bc0a1bf9a11c1a4c62e
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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