Potassium Permanganate → HCID 14990577, compound

HRID 2248316Notes

Reaction equation

HRID 2248316 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH3:7][N:8]1[C:12]2[C:13]([CH2:17][OH:18])=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1>ClCCl>[CH3:7][N:8]1[C:12]2[C:13]([CH:17]=[O:18])=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 14990571HCID 14990571, compound

Product 1

HCID 14990577HCID 14990577, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 7.4 parts of potassium permanganate, 0.6 parts of 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl] ethamamine and 130 parts of dichloromethane was added dropwise a solution of 7.6 parts of 1-methyl-1H-benzotriazole-7-methanol in dichloromethane. Upon complete addition, stirring was continued for 2 hours. The reaction mixture was filtered over diatomaceous earth and washed with dichloromethane. The organic layer was washed with 30 parts of a hydrochloric acid solution 2N and then with a sodium carbonate solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.5 parts (46.6%) of 1-methyl-1-H-benzotriazole-7-carboxaldehyde; mp. 126° C. (int. 18).

Workup

  1. additionUpon complete addition
  2. filtrationThe reaction mixture was filtered over diatomaceous earth
  3. washwashed with dichloromethane
  4. washThe organic layer was washed with 30 parts of a hydrochloric acid solution 2N
  5. dry with materialwith a sodium carbonate solution, dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-3bd94976340f4420836fbd0f8d7f1ef4
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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