N-[4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide → 6-Methyl-4-(pentan-3-YL)pyridazin-3-amine

HRID 226005Notes

Reaction equation

HRID 226005 reaction equation
[CH2:1]([CH:3]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[N:8][C:7]=1[NH:13]C(=O)C(C)(C)C)[CH2:4][CH3:5])[CH3:2]>Cl>[CH2:1]([CH:3]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[N:8][C:7]=1[NH2:13])[CH2:4][CH3:5])[CH3:2]

Participants

3

Reactant 1

HCID 68842351N-[4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide

Product 1

HCID 534216106-Methyl-4-(pentan-3-YL)pyridazin-3-amineYield 82.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

Dissolve 12.0 g (45 mmol) of N-[4-(1-ethyl-propyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide in 60 ml of concentrated hydrochloric acid. Heat to 95° C. in a sealed flask for 2 h. Work up by pouring over ice and extracting with ethyl acetate three times. Discard the organic and adjust pH of aqueous to basic using 2N sodium hydroxide. Extract basic solution with ethyl acetate five times. Dry over magnesium sulfate, filter, and evaporate to obtain 6.68 g (37 mmol, 81.0%) of the title compound as brownish oil. 1H-NMR (DMSO-d6): δ 6.95 (s, 1H); 5.89 (s, br, 2H); 2.52-2.56 (m, 1H); 2.34 (s, 3H); 1.44-1.58 (m, 4H); 0.72 (t, J=7.04 Hz, 6H) ppm. MS/ES+=180 (100%, M+1).

Workup

  1. additionby pouring over ice
  2. extractionextracting with ethyl acetate three times
  3. extractionExtract basic solution with ethyl acetate five times
  4. dry with materialDry over magnesium sulfate
  5. filtrationfilter
  6. customevaporate

Sources & evidence

ORD record
ord-0a7e55e356254d93841da9005be59273
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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