Hydrochloric Acid → HCID 14810905, compound

HRID 1710103Notes

Reaction equation

HRID 1710103 reaction equation
[I-].[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][N+:20]([CH3:23])=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[CH:4]1.[BH4-].[Na+].[ClH:26]>C(O)C.O>[ClH:26].[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[O:13][C:14]([C:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH:18]=3)=[N:15][N:16]=2)=[CH:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14810902HCID 14810902, compound

Product 1

HCID 14810905HCID 14810905, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-[2-(1-methylindol-3-yl)-1,3,4-oxadiazol-5-yl]-1-methylpyridinium iodide (1.0 g) was suspended in a mixture of ethanol (50 ml) and water (5 ml) with vigorous stirring. NaBH4 (200 mg) was added portionwise until the solution was clear and colourless. The solution was stirred for one hour at room temperature. 2N Hydrochloric acid (10 ml) was added to quench the excess NH4OH, followed by 0.88 NH3 to pH 12, the solution was then extracted with dichloromethane (4×100 ml), dried over MgSO4 and evaporated to dryness. The residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98). The isolated product was treated with an excess of ethereal HCl, recrystallisation from absolute methanol afforded the title compound as a white solid m.p. 245°-250° C. Found: C, 61.35; H, 5.85; N, 16.74; C17H18N4OCl requires C 61.72; H, 5.78; N, 16.93%; δH (360 MHz, D2O 2.67 (2H, bm, CH2 --N--CH3), 3.07 (3H, s, N--CH3), 3.4 (2H, brm, CH2N--CH3), 3.55 (3H, s, N--CH3), 3.48 (2H, brm, CH2CH2N), 6.27 (1H, brm, C=CH--CH2), 7.09 (2H, brm, H-5,6), 7.11 (1H, d, J=5 Hz, H-4), 7.22 (1H, s, H-2), 7.35 (1H, d, J=5 Hz, H-7); m/z 294 (M+ free base, 100%), 158 (40), 110 (30), 94 (30), 77 (10).

Workup

  1. customto quench the excess NH4OH
  2. extractionthe solution was then extracted with dichloromethane (4×100 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98)
  6. additionThe isolated product was treated with an
  7. customexcess of ethereal HCl, recrystallisation from absolute methanol

Sources & evidence

ORD record
ord-ba36dde4569c45c683d599ad079c23dc
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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