Sodium Hydroxide → HCID 19434249, compound

HRID 1769170Notes

Reaction equation

HRID 1769170 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:6][CH:7]=1.[Br:22]Br.[OH-].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[C:11]=2[Br:22])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 19434263HCID 19434263, compound2×

Product 1

HCID 19434249HCID 19434249, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

3-Amino-6-(3,4,5-trimethoxybenzyloxy)pyridazine (Intermediate 1, 2.91 g, 10 mMol) in acetic acid (20 ml) was treated dropwise with a solution of bromine (1.59 g, 10 mMol) in acetic acid (2 ml) over 5 minutes. After 0.5 hours, the mixture was filtered to give a cream solid which was suspended in water and basified with sodium hydroxide solution. The mixture was extracted with chloroform and the extracts were washed with water, dried (Na2SO4) and evaporated in vacuo to yield a cream solid which was recrystallised from toluene to give the title compound (2.76 g) as cream needles, m.p. 160°-161° C., NMR δH(CDCl3) 6.93(1H,s,ArH) 6.91(1H,JAB,8.8 Hz,5H), 6.80(1H,JAB,8.8 Hz,4H), 5.49(2H,s,CH2), 4.95(2H, brs,NH2), 3.91(3H,s,OCH3), 3.90(3H,s,OCH3) and 3.89(3H,s,OCH3 ).

Workup

  1. filtrationthe mixture was filtered
  2. customto give a cream solid which
  3. extractionThe mixture was extracted with chloroform
  4. washthe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customto yield a cream solid which
  8. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-19e0fa11688342d5b152090d80bb3f80
Source dataset
uspto-grants-1995_01
Patent number
US05380759

Reaction notes

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