Bromine → HCID 18438121, compound

HRID 1643195Notes

Reaction equation

HRID 1643195 reaction equation
BrBr.[CH2:3]([CH:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][NH:10][C:9](=[O:19])[CH2:8]1)[CH2:4][CH2:5][CH3:6]>CC(O)=O>[CH2:3]([C:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][NH:10][C:9](=[O:19])[CH:8]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 18438122HCID 18438122, compound

Product 1

HCID 18438121HCID 18438121, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.94 ml, 18.2 mmol) in HOAc (10 mL) is added dropwise to a solution of 5-butyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one (3-8g, 16.5 mmol) in HOAc (40 mL) at 80° C. After the addition is complete, the heating is continued for 30 minutes and the solvent is evaporated in vacuo. The residue is partitioned between saturated aqueous NaHCO3 solution (50 mL) and EtOAc (50 mL) and the organic layer washed with water (35 mL), brine (35 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides the desired product as a yellow solid. LC-MS (M+1) 229. 1H NMR (δ, CDCl3) 12.39 (s, 1H), 7.39-7.48 (m, 5H), 6.83 (s, 1H), 2.41 (t, J=7.2 Hz, 2H), 1.20-1.43 (m, 4H), 0.77 (t, J=7.7 Hz, 3H).

Workup

  1. additionAfter the addition
  2. customthe solvent is evaporated in vacuo
  3. customThe residue is partitioned between saturated aqueous NaHCO3 solution (50 mL) and EtOAc (50 mL)
  4. washthe organic layer washed with water (35 mL), brine (35 mL)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-285b44ae138548028b75c9d455ec025f
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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