Sodium Hydroxide → HCID 23155492, compound

HRID 2080823Notes

Reaction equation

HRID 2080823 reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][C:8]1[N:9]([CH2:19][CH2:20][CH3:21])[C:10]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:2][CH3:3].[OH-].[Na+]>[Ni].C(O)C>[NH2:18][CH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][N:4]([CH2:22][CH2:23][CH3:24])[CH2:1][CH2:2][CH3:3])[N:9]([CH2:19][CH2:20][CH3:21])[C:10]=2[CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23155406HCID 23155406, compound

Product 1

HCID 23155492HCID 23155492, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

An ethanol solution (12 ml) containing the compound (0.363 g) obtained in Example 46-5 was added with a 1 mol/l sodium hydroxide aqueous solution (3.6 ml) and added with Raney nickel (120 mg). The whole was stirred for 6 hours under a hydrogen atmosphere. The catalyst was removed by filtration through Celite and the solvent was distilled off. After that, the resultant was partitioned into chloroform and water. The solution was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous magnesium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (0.244 g) as a colorless liquid.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. distillationthe solvent was distilled off
  3. customAfter that, the resultant was partitioned into chloroform and water
  4. washThe solution was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe residue obtained
  7. distillationby distilling the solvent
  8. customoff was purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-92ae91202af3414492e8d56741167352
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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