N-[4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide → 6-Methyl-4-(pentan-3-YL)pyridazin-3-amine
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
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
N-[4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide (12.0 g, 45 mmol) is dissolved in 60 mL of concentrated hydrochloric acid. The reaction mixture is heated to 95° C. in a sealed flask for 2 hours. The reaction is worked up by pouring over ice and extracting with ethyl acetate three times. The organic layer is discarded, and the pH of the aqueous layer is adjusted using 2 N sodium hydroxide. The basic solution is extracted with ethyl acetate five times. The organic extracts are combined, dried over magnesium sulfate, filtered, and evaporated to obtain 6.68 g (37 mmol, 81%) of the title compound as a 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
- additionby pouring over ice
- extractionextracting with ethyl acetate three times
- extractionThe basic solution is extracted with ethyl acetate five times
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-bb47aa62f2e84ee7b7abae4b0532ad2c
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612067B2
Reaction notes
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