Hexamethylenetetramine → 7-Methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinoline-8-carboxaldehyde

HRID 1740733Notes

Reaction equation

HRID 1740733 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[N:13]=[N:14][N:15]=[C:8]1[CH2:7][CH2:6]2.C1N2CN3CN(C2)CN1C3.[C:26](O)(C(F)(F)F)=[O:27]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:26]=[O:27])[N:9]1[N:13]=[N:14][N:15]=[C:8]1[CH2:7][CH2:6]2

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 131951067-Methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinoline

Product 1

HCID 221329187-Methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinoline-8-carboxaldehydeYield 50%

Procedure

To a stirred solution of Compound 1 (160 mg, 0.79 mmol) in TFA (16 ml) was added hexamethylenetetramine (1.1 g, 7.9 mmol), and refluxed for 3 days. The solvent was evaporated, and the residue was diluted with AcOEt. This organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 2 (90 mg, 0.39 mmol, 50%) as a white solid.

Workup

  1. temperaturerefluxed for 3 days
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with AcOEt
  4. washThis organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-d7a78e4fb7984f1cbbff1b4a9565ae11
Source dataset
uspto-grants-1999_10
Patent number
US05972930

Reaction notes

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