Ammonium formate → HCID 14723691, compound

HRID 1608303Notes

Reaction equation

HRID 1608303 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:30])[CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)[CH:12]=[N:11]1)[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[CH:12]=[N:11][N:10]([CH2:9][C:8]([NH:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:31][CH3:32])=[O:30])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 14723690HCID 14723690, compound

Product 1

HCID 14723691HCID 14723691, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 43.7 g (0.1 mol) of N-[3-(diethylamino)propyl]-4-(4-nitrophenyl)-5-phenyl-1H-pyrazole-1-acetamide of example 45 in 200 mL of methanol was refluxed for 2 hr with 4 g of 10% palladium on charcoal and 30 g of ammonium formate. The catalyst was filtered off and the filtrate was stripped. The residue was distributed between aqueous NaOH and 1:1 THF-ether. The ether layer was dried over magnesium sulfate, stripped and recrystallized from methyl t-butyl ether to yield 38.9 g of product, mp 75°-76° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. customrecrystallized from methyl t-butyl ether

Sources & evidence

ORD record
ord-58cbbc9cb72f473787d77859c7b66de4
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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