Sodium Hydroxide → HCID 53353686, compound

HRID 2174534Notes

Reaction equation

HRID 2174534 reaction equation
Cl[C:2]1[C:3](=[O:20])[N:4]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[N:5]=[CH:6][C:7]=1[NH:8][CH3:9].[OH-].[Na+].[H][H]>C(O)C.[Pd]>[CH3:9][NH:8][C:7]1[CH:6]=[N:5][N:4]([CH:10]2[CH2:15][C:14]([CH3:16])([CH3:17])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[C:3](=[O:20])[CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53353683HCID 53353683, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53353686HCID 53353686, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Chloro-5-methylamino-2-(3,3,5,5-tetramethylcyclohexyl)pyridazin-3-one (0.15 g, 0.5 mmoles) was dissolved in ethanol (20 mL) and 1M sodium hydroxide (1 ml) was added. 10% Palladium on charcoal (40 mg) was added and the reaction mixture was stirred overnight under a balloon of hydrogen. Filtered off the catalyst and evaporated to a low bulk. Partitioned between water and ethyl acetate, separated and dried over magnesium sulphate. Evaporated to give the required product as a buff solid. (0.125 g, 94%). 1H NMR (300 MHz CDCl3) 7.32 (d, 1H, J=3 Hz), 5.7 (d, 1H, J=3 Hz), 5.3 (m, 1H), 4.2 (brs, 1H), 2.85 (d, 3H, J=5 Hz), 1.55 (m, 4H), 1.3 (m, 1H), 1.15 (m, 1H), 1.15 (s, 6H), 0.95 (s, 6H).

Workup

  1. filtrationFiltered off the catalyst
  2. customevaporated to a low bulk
  3. customPartitioned between water and ethyl acetate
  4. customseparated
  5. dry with materialdried over magnesium sulphate
  6. customEvaporated

Sources & evidence

ORD record
ord-4bb4ca08512a4345a03e2d4c69c9807c
Source dataset
uspto-grants-2015_06
Patent number
US09062004B2

Reaction notes

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