Ethyl Acetoacetate → HCID 616235, compound

HRID 489724Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]N)=[CH:14][CH:13]=1>C(O)(=O)C>[CH2:8]([O:7][C:1]([C:2]1[C:16]2[C:15](=[CH:14][CH:13]=[C:12]([O:11][CH3:10])[CH:17]=2)[NH:18][C:3]=1[CH3:5])=[O:6])[CH3:9]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl acetoacetate (5.5 ml, 43.15 mmol) was added into a solution of (4-methoxy-phenyl)-hydrazine (5.0 g, 28.63 mmol) in glacial acetic acid (500 ml) at room temperature. The mixture was heated at 110° C. for 2 hours, and kept at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane and 1 N sodium hydroxide solution. The organic extract was dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 2% methanol in dichloromethane to give 5-Methoxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester as a dark solid, (3.18 g, 47%). 1H NMR (CDCl3) δ:1.44 (t, 3H, J=7.1 Hz), 2.70 (s, 3H), 3.87 (s, 1H), 4.39 (q, 2H, J=7.1 Hz), 6.82(dd, 1H, J=8.8 Hz, 2.5 Hz), 7.17 (d, 1H, J=8.8 Hz), 7.63 d, 1H, J=2.5 Hz), 8.38 (bs, 1H). M−H: 232.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was partitioned between dichloromethane and 1 N sodium hydroxide solution
extractionThe organic extract
dry with materialwas dried (anhydrous sodium sulfate)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography over silica gel eluting with 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-6229788bf42b4f0ebfe80b490f07ddc3
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979696B2

Reaction notes

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