Methanol → HCID 69198972, compound

HRID 2376245Notes

Reaction equation

HRID 2376245 reaction equation
[C:1]1([CH3:31])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:19][CH:20]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[CH2:21]C#N)=[N:8]2)=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:37](=[O:40])(O)[O-:38].[Na+].[CH3:42]O>>[CH3:42][O:38][C:37](=[O:40])[CH2:21][CH:20]([C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=1)[CH2:19][C:9]1[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:31])=[CH:2][CH:3]=2)[N:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22171014HCID 22171014, compound

Product 1

HCID 69198972HCID 69198972, compoundYield 82%

Procedure

To a flask were added 4-(1,5-di-p-tolyl-1H-pyrazol-3-yl)-3-m-tolyl-butyronitrile (100 mg, 0.24 mmol), concd sulfuric acid (1.5 mL) and methanol (1.5 mL). The mixture was heated to reflux for 24 h. The reaction mixture was cooled to room temperature, poured into ice (20 g) and neutralized with satd sodium bicarbonate. The resulting solution was extracted with diethyl ether (3×10 mL), and the combined organic extracts were washed with water (10 mL) then brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude residue was purified by reversed-phase HPLC yielding the desired ester (86 mg, 82%). HPLC: Rt=3.43 (Method B). MS (ESI): mass calculated for C29H30N2O2, 438.23; m/z found, 439.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.19 (t, J=7.4 Hz, 1H), 7.01-7.13 (m, 11H), 6.15 (s, 1H), 3.56 (s, 3H), 3.54-3.52 (m, 1H), 3.11-3.08 (m, 2H), 2.77-2.75 (m, 2H), 2.36 (s, 3H), 2.32 (s, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. extractionThe resulting solution was extracted with diethyl ether (3×10 mL)
  4. washthe combined organic extracts were washed with water (10 mL)
  5. dry with materialbrine (10 mL), dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-065ee98191bc4e739db9bcadab95a9d1
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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