Perchloric Acid → (7-methyl-1H-indazol-5-yl)-acetaldehyde

HRID 2099735Notes

Reaction equation

HRID 2099735 reaction equation
C[O:2][CH:3]=[CH:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][N:9]=[CH:8]2.Cl(O)(=O)(=O)=O>O1CCCC1.O.C(OCC)(=O)C>[CH3:14][C:12]1[CH:13]=[C:5]([CH2:4][CH:3]=[O:2])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2

Participants

6

Reactant 2

HCID 24247Perchloric Acid2×HCID 690713565-(2-methoxy-vinyl)-7-methyl-1H-indazole

Product 1

HCID 57794606(7-methyl-1H-indazol-5-yl)-acetaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-methoxy-vinyl)-7-methyl-1H-indazole (365 mg, 1.94 mmol, 1.0 equiv.) in tetrahydrofuran (8 mL) was added 60% perchloric acid (0.63 mL, 3 equiv) in one portion under nitrogen. After 2 h, more perchloric acid (0.63 mL) was added. After 4 h, LCMS indicated that no starting material was present. The reaction mixture was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with water (3×). The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give an off-white solid. The crude material was carried on without further purification. MS (ESI) [M+H]+=175.

Workup

  1. waitAfter 4 h
  2. customThe layers were separated
  3. washthe organic layer was washed with water (3×)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an off-white solid
  8. customThe crude material was carried on without further purification

Sources & evidence

ORD record
ord-ecfc209e6f2d414c95bff7906908e453
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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