Sodium Hydroxide → HCID 19434249, compound

HRID 1735723Notes

Reaction equation

HRID 1735723 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 (1 H, s, ArH), 6.91 (1 H, JAB, 8.8 Hz, 5 H), 6.80 (1 H, JAB, 8.8 Hz, 4 H), 5.49 (2 H, s, CH2), 4.95 (2 H, brs, NH2), 3.91 (3 H, s, OCH3), 3.90 (3 H, s, OCH3) and 3.89 (3 H, 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-0f3187b1358742578d78d4c210de507f
Source dataset
uspto-grants-1996_07
Patent number
US05538970

Reaction notes

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