Potassium Permanganate → HCID 23503285, compound

HRID 1835143Notes

Reaction equation

HRID 1835143 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[OH:7][CH:8]([C:19]1[S:33][C:22]2[C:23]([CH2:29][CH:30]([CH3:32])[CH3:31])=[N:24][N:25]([CH3:28])[C:26](=[O:27])[C:21]=2[CH:20]=1)[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>ClCCl>[CH3:28][N:25]1[C:26](=[O:27])[C:21]2[CH:20]=[C:19]([C:8]([C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=[CH:11][CH:10]=3)=[O:7])[S:33][C:22]=2[C:23]([CH2:29][CH:30]([CH3:32])[CH3:31])=[N:24]1

Participants

4

Reactant 2

HCID 516875Potassium Permanganate2×HCID 23503229HCID 23503229, compound

Product 1

HCID 23503285HCID 23503285, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium permanganate (0.335 g) and 18 crown-6 (10 mg) were added to a solution of 2-[1-hydroxy-1-(1-naphthalenyl)methyl]-5-methyl-7-(2methylpropyl)thieno[2,3-d]pyridazin-4(5H)-one (example 7, 0.40 g) in dichloromethane (30 ml) at room temperature. After 1 hour, further potassium permanganate (0.30 g) was added and stirring was continued for a further hour. The mixture was filtered, diluted with dichloromethane (70 ml), washed twice with water then with brine, then dried, filtered and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate:isohexane (1:2), to give the title compound (0.14 g). This was purified further by preparative normal-phase HPLC with gradient ethyl acetate/isohexane elution.

Workup

  1. waitwas continued for a further hour
  2. filtrationThe mixture was filtered
  3. additiondiluted with dichloromethane (70 ml)
  4. washwashed twice with water
  5. dry with materialwith brine, then dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate:isohexane (1:2)

Sources & evidence

ORD record
ord-ab617a17871b48a8890e233bc1b4f0bf
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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