Methyl pyruvate → HCID 18549820, compound
Reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=O.COC(OC)[N:11]([CH3:13])C.Cl.[C:17]1([CH3:25])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23]N>C(O)(=O)C>[CH3:25][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[C:2]([C:1]([O:6][CH3:7])=[O:5])=[CH:4][CH:13]=[N:11]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A neat mixture of methyl pyruvate (11.37 mL, 125.9 mmol) and dimethylformamide dimethylacetal (16.72 mL, 125.9 mmol) was stirred at 80° C. for 24 h. The mixture was cooled and concentrated. A portion of the residue (4.00 g, 25.45 mmol) was dissolved in 50 mL of glacial acetic acid and then there was added o-tolylhydrazine hydrochloride (4.44 g, 27.99 mmol). This mixture was stirred at 100° C. for 18 h and then was cooled and concentrated. The residue was dissolved in ethyl acetate, washed with sat'd aq sodium carbonate and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (elution with 2:1 hexanes/ethyl acetate) to afford 3.0 g (55%) of the title compound. 1H NMR (CDCl3) δ7.70 (d, 1H), 7.4-7.2 (m, 4H), 7.00 (d, 1H), 3.71 (s, 3H), 2.00 (s, 3H).
Workup
- temperatureThe mixture was cooled
- concentrationconcentrated
- stirringThis mixture was stirred at 100° C. for 18 h
- temperaturewas cooled
- concentrationconcentrated
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with sat'd aq sodium carbonate and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by flash chromatography (elution with 2:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-26e9b545e63848e68c6d6cf3a5e03e53
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548525B2
Reaction notes
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