Hydrochloric Acid → 3-Pyridazinamine, 6-methyl-4-(1-methylethyl)-

HRID 226026Notes

Reaction equation

HRID 226026 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[N:6][C:5]=1[NH:11]C(=O)C(C)(C)C)[CH3:3].Cl>>[NH2:11][C:5]1[N:6]=[N:7][C:8]([CH3:10])=[CH:9][C:4]=1[CH:2]([CH3:1])[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68858996N-[4-(1-methylethyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide

Product 1

HCID 451166433-Pyridazinamine, 6-methyl-4-(1-methylethyl)-Yield 67%

Procedure

N-[4-(1-methylethyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide (1.38 g, 5.87 mmol) is treated with HCl 0 (10 mL), and refluxed for 3 h. It is cooled to rt, poured into ice-H2O (30 mL); extracted with EtOAc (2×30 mL). The aqueous layer is treated with 5 M NaOH to adjust the pH to 8-9. It is then extracted with EtOAc (3×50 mL); dried with Na2SO4, filtered and concentrated gives the title compound (0.59 g, 3.91 mmol, 67%). %). 1H NMR (CDCl3): δ 1.28 (d, J=7.0 Hz, 6H), 2.51 (s, 3H), 2.72-2.83 (m, 1H), 5.95 (bs, 2H), 7.02 (s, 1H) ppm. ES-MS (m/z): calcd for C8H13N3 (M+H)+: 152.2. found: 152.1.

Workup

  1. temperaturerefluxed for 3 h
  2. extractionextracted with EtOAc (2×30 mL)
  3. additionThe aqueous layer is treated with 5 M NaOH
  4. extractionIt is then extracted with EtOAc (3×50 mL)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-35f6e308f3c14c7eb58dd5fe0867d5aa
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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