Hexanal → ethyl 3-butyl-1H-indole-5-carboxylate

HRID 14211

Reaction equation

Cl.[NH:2]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)N.[CH:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C.O>[CH2:17]([C:16]1[C:14]2[C:4](=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:13]=2)[NH:2][CH:15]=1)[CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of ethyl 4-hydrazinobenzoate hydrochloride (10 gm) in ethanol:water (5:1 100 mL) was added hexanal (4.62 gm). The mixture was refluxed at 100° C. for 3 h. The solvents were removed and toluene (100 mL) and p-toluene sulfonic acid (0.1 g) were added. The mixture was refluxed at 120° C. for 18 h, cooled to room temperature and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 90:9:1 (hexanes: methylene chloride: ethyl acetate) as eluent to give 0.8 g of the title compound: 1H NMR (CDCl3) δ 0.957, 1.44, 1.72, 2.78, 4.40, 7.02, 7.34, 7.90, 8.13, 8.38.

Workup

customThe solvents were removed
additiontoluene (100 mL) and p-toluene sulfonic acid (0.1 g) were added
temperatureThe mixture was refluxed at 120° C. for 18 h
temperaturecooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-24d89a1243144378823b3d79fa8c8f3c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727997B2

Linked notes

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