Potassium Carbonate → HCID 68029870, compound

HRID 1808865Notes

Reaction equation

HRID 1808865 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[CH:11][N:12]([CH3:16])[C:13]=1[CH:14]=[O:15].C(=O)([O-])[O-:18].[K+].[K+].[K].[O-][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[CH:11][N:12]([CH3:16])[C:13]=1[C:14]([OH:18])=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516875Potassium PermanganateHCID 5462222PotassiumHCID 84126197HCID 84126197, compound

Product 1

HCID 68029870HCID 68029870, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a soln. of 4-(2-methoxyphenyl)-1-methyl-1H-imidazole-5-carbaldehyde (78 mg, 0.361 mmol) in acetone (5 ml) and water (1 ml) was added potassium carbonate (100 mg, 0.721 mmol). After potassium was dissolved, KMnO4 (123 mg, 0.776 mmol) was added at r.t. The mixture was stirred for 24 hrs. LC/MS showed the completion. The mixture was filtered through celite, washed w/water. The actone was evaporated from the filtrate which was extracted with EtOAc (2×). The aq. layer was acidified w/HOAc to PH=5, reduced the volume to half volume, feezed and lyphilized to leave solid, which was purified by Pre-HPLC to afford the title compound (41 mg, 0.173 mmol, 48% yield). 1H-NMR (MeOD), δ: 8.06 (s, 1H), 7.41-7.36 (m, 2H), 7.05-6.99 (m, 2H), 3.98 (s, 3H), 3.80 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed w/water
  3. customThe actone was evaporated from the filtrate which
  4. extractionwas extracted with EtOAc (2×)
  5. customto leave solid, which
  6. customwas purified by Pre-HPLC

Sources & evidence

ORD record
ord-787db8ed90fb45fea46bd7d9ba5a424e
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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