HCID 15907519, compound → HCID 15907520, compound

HRID 429810Notes

Reaction equation

HRID 429810 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[C:5]([N:13]=O)[C:4]([CH3:15])=[N:3]1>[Pd].CCOC(C)=O>[CH3:10][C:9]([CH3:12])([CH3:11])[CH2:8][NH:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([CH3:15])[C:5]=1[NH2:13]

Participants

4

Reactant 1

HCID 15907519HCID 15907519, compound

Product 1

HCID 15907520HCID 15907520, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

(2,5-Dimethyl-4-nitroso-2H-pyrazol-3-yl)-(2,2-dimethyl-propyl)-amine (3.44 g, 16.36 mmol), 400 mg of 10% Pd/C and 60 mL EtOAc were placed under a balloon of H2 and stirred at 23° C. After 4 h, the reaction mixture was filtered through Celite and evaporated to an orange oil. Flash chromatography on silica gel, eluting with CHCl3/MeOH (20/1), gave a yellow solid. Recrystallization from hot hexanes/EtOAc gave 2.86 g (14.57 mmol, an 89% yield) of the title compound as an off-white crystalline solid. mp: 65-69° C.; 1H NMR (300 MHz, CDCl3): δ1.00 (s, 9H), 1.65 (brs, 2H), 2.13 (s, 3H), 2.77 (brs, 2H), 2.89 (brs, 1H), 3.62 (s, 3H); IR (KBr, cm−1): 3347-3204brs, 2952s, 2903w, 1599m, 1528m, 1495m, 1477m, 1378m, 1316m; MS (ES) m/z (relative intensity): 197 (M++H, 100). Anal. Calcd. for C10H20N4: C, 61.19; H, 10.27; N, 28.54. Found: C, 56.19; H, 10.56; N, 26.37

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. customevaporated to an orange oil
  3. washFlash chromatography on silica gel, eluting with CHCl3/MeOH (20/1)
  4. customgave a yellow solid
  5. customRecrystallization from hot hexanes/EtOAc
  6. customgave 2.86 g (14.57 mmol

Sources & evidence

ORD record
ord-c91de20c77104b459849937a031c33f6
Source dataset
uspto-grants-2001_11
Patent number
US06319941B1

Reaction notes

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