ChemicalBook CAS DataBase List 1-ethyl-1H-indole-4-carbaldehyde

1-ethyl-1H-indole-4-carbaldehyde synthesis

1synthesis methods

Product Name:1-ethyl-1H-indole-4-carbaldehyde
CAS Number:894852-86-9
Molecular formula:C11H11NO
Molecular Weight:173.21

1074-86-8

75-03-6

894852-86-9

a) Synthesis of 1-ethyl-1H-indole-4-carboxaldehyde: Sodium hydride (827 mg, 60% dispersion in oil, 20.7 mmol) was added batchwise to an anhydrous N,N-dimethylformamide (DMF, 6.5 mL) solution of 1H-indole-4-carboxaldehyde (2.00 g, 13.8 mmol) under argon protection. The reaction mixture was stirred at room temperature for 30 min. Subsequently, ethidium iodide (2.22 mL, 27.5 mmol) was slowly added dropwise and stirring was continued for 12 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give an orange oily crude product. Purification by silica gel column chromatography (elution gradient: dichloromethane to 5% methanol/dichloromethane) afforded the target compound 1-ethyl-1H-indole-4-carbaldehyde (2.43 g, 99% yield) as a yellow oil. Its nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, DMSO-d6) data were as follows: δ 10.19 (s, 1H), 7.88 (d, J = 8.1 Hz, 1H), 7.68-7.64 (m, 2H), 7.37-7.32 (m, 1H), 7.08 (d, J = 3.0 Hz, 1H), 4.28 (q, J = 7.2 Hz, 2H), 1.36 (t, J = 7.2 Hz, 3H).

1074-86-8 Synthesis

1074-86-8
297 suppliers
$10.00/1g

75-03-6
366 suppliers
$11.00/5g

894852-86-9
30 suppliers
$45.00/50mg

Yield:894852-86-9 99%

Reaction Conditions:

Stage #1: 4-formyl indolewith sodium hydride in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: ethyl iodide in N,N-dimethyl-formamide at 20; for 12 h;

Steps:

75.a

a) l-ethyl-lH-indole-4-carbaldehvde; To a solution of lH-indole-4-carbaldehyde (2.00 g, 13.8 mmol) in anhydrous DMF (6.5 niL) was added sodium hydride (827 mg of 60% dispersion in oil, 20.7 mmol). The mixture was stirred for 30 min at room temperature. Ethyl iodide (2.22 mL, 27.5 mmol) was then added and the reaction mixture was stirred for 12 h at room temperature. Water was added (100 mL) and the mixture was extracted with ethyl acetate (3x 100 mL). Combined organic layers were washed with brine (100 mL), dried over Na₂SO₄, filtered and concentrated to an orange oil. Purification by column chromatography (silica gel, gradient elution Of CH₂Cl₂ to 5% MeOH/CH₂Cl₂) gave the title compound (1-ethyl-lH- indole-4-carbaldehyde) (2.43 g, 99%) as a yellow oil: ¹H NMR (300 MHz, OMSOd₆) δ 10.19 (s, IH), 7.88 (d, J= 8.1 Hz, IH), 7.68-7.64 (m, 2H), 7.37-7.32 (m, IH), 7.08 (d, J= 3.0, IH), 4.28 (q, J= 7.2 Hz, 2H), 1.36 (t, J= 7.2 Hz, 3H).

References:

WO2007/53131,2007,A2 Location in patent:Page/Page column 179-180

1-ethyl-1H-indole-4-carbaldehyde Related Search:

1-(PHENYLMETHYL)-1H-INDOLE-4-CARBOXALDEHYDE