Hydrochloric Acid → 3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol

HRID 1005373Notes

Reaction equation

HRID 1005373 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12]N)=[CH:8][CH:7]=2)[CH:5]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.Cl>O1CCOCC1>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[C:10]3[C:9](=[CH:8][CH:7]=2)[NH:12][CH:19]=[C:18]3[CH2:17][CH2:16][CH2:15][OH:14])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 51624184-(4-hydrazinylphenyl)-4H-1,2,4-triazole

Product 1

HCID 106339143-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(1,2,4-triazol-4-yl)phenylhydrazine (25 g, 143 mmol) in dioxan (250 ml) was treated with dihydropyran (24 g, 286 mmol) followed by 1M hydrochloric acid (150 ml) and heated at reflux for 18 hours. The solvent was evaporated, treated with toluene then reevaporated. Inorganic solids were removed by treating the residue with a mixture of methanol and acetonitrile. The mother liquors were purified by column chromatography on silica using dichloromethane/methanol (9:1→4:1) as the eluant. The compound was recrystallised from methanol/acetonitrile to afford the title compound a a colourless solid (10.24 g, 30%), mp 205-207° C. (Found: C, 64.37; H, 5.76; N, 22.83. C13H14N4O requires C, 64.45; H, 5.82; N, 23.13%). MS, ES+, m/z=243 for (M+H)+ ; δH (360 MHz, DMSO-d6) 1.81 (2H, quintet, J=8 Hz), 2.75 (2H, t, J=8 Hz), 3.46 (2H, dt, J1 =5, J2 =8 Hz), 4.43 (1H, t, J=5 Hz), 7.26 (1H, d, J=2 Hz), 7.29 (1H, dd, J1 =2, J2 =9 Hz), 7.47 (1H, d, J=9 Hz), 7.77 (1H, d, J=2 Hz), 9.01 (2H, s), 11.05 (1H, br s).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. additiontreated with toluene
  5. customthen reevaporated
  6. customInorganic solids were removed
  7. additionby treating the residue
  8. additionwith a mixture of methanol and acetonitrile
  9. customThe mother liquors were purified by column chromatography on silica
  10. customThe compound was recrystallised from methanol/acetonitrile

Sources & evidence

ORD record
ord-f5b08301b40c4dc7bb09c595c6109f8d
Source dataset
uspto-grants-2000_04
Patent number
US06054469

Reaction notes

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