HCID 16638017, compound → HCID 20269042, compound

HRID 485685Notes

Reaction equation

HRID 485685 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[NH:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH:7]=1)=[O:5])[CH3:2]>O1CCCC1.C.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:10](=[O:11])[NH:9]2)=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 16638017HCID 16638017, compound

Product 1

HCID 20269042HCID 20269042, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 297MethaneCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Ethoxycarbonyl-2-(4-nitrophenyl)-3-pyrazolin-5-one (5.66 g, 20.43 mmol) in distilled tetrahydrofuran (250 ml) containing 10% Palladium|charcoal catalyst (1.13 g) was hydrogenated at atmospheric pressure for 11/2 hours at 0° C. followed by 2 hours at room temperature. The catalyst was then removed by filtration through celite and the celite washed with tetrahydrofuran. The filtrate was then evaporated to dryness to yield the title compound (5.0 g) after trituration (Ether; hexane), νmax (Nujol) 1693, 1675, 1630, 1599, 1585, 1290, 835, 775 cm-1 δ(D6 -Acetone) 1.37 (3H, t, J7 Hz, --OCH2CH3), 3.10 (2H, bs, --NH2), 4.36 (2H, q,J7Hz, --OCH2CH3), 6.80 (2H, d, J9Hz, protons o--NH2), 7.53 (2H, d, J9 Hz, protons m--NH2), 8.35 (1H, s, C3 pyrazole proton). Found: M+, 247.0954; C12H13N3O3 requires M, 247.0956.

Workup

  1. custom2 hours
  2. customat 0° C.
  3. customThe catalyst was then removed by filtration through celite
  4. washthe celite washed with tetrahydrofuran
  5. customThe filtrate was then evaporated to dryness

Sources & evidence

ORD record
ord-d19da59425d2428f827a9696372f1532
Source dataset
uspto-grants-1985_08
Patent number
US04537886

Reaction notes

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