Tetramethoxypropane → 5-(1H-pyrazol-1-yl)isoquinoline

HRID 532890Notes

Reaction equation

HRID 532890 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2)[NH2:2].CO[CH:15](OC)[CH2:16][CH:17](OC)OC>CCO.C(Cl)Cl>[N:1]1([C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][N:7]=[CH:8]3)[CH:17]=[CH:16][CH:15]=[N:2]1

Participants

5

Reactant 2

HCID 66019TetramethoxypropaneHCID 132664235-Hydrazinylisoquinoline

Product 1

HCID 867113425-(1H-pyrazol-1-yl)isoquinolineYield 73.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-hydrazinylisoquinoline (22.0 g, 112 mmol) in EtOH (300 mL) was treated with 1,1,3,3-tetramethoxypropane (27.7 g, 169 mmol) and the mixture was heated to 100° C. for 10 h. The reaction mixture was then concentrated in vacuo and the residue obtained taken up in DCM (500 mL) and washed with a saturated aqueous solution of NaHCO3 gas formation. The aqueous layer was extracted twice with DCM and the combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, DCM/MeOH 95:5 to DCM/MeOH 9:1) to give the title compound (16.1 g). UPLC-MS: MS 196.1 (M+H+); UPLC rt 0.62 min.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue obtained
  3. washwashed with a saturated aqueous solution of NaHCO3 gas formation
  4. extractionThe aqueous layer was extracted twice with DCM
  5. dry with materiallayers were then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, DCM/MeOH 95:5 to DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-12dc6e020a92437a830fbc4049254085
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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