Methyl 1-Methyl-1H-indole-4-carboxylate

Methyl 1-Methyl-1H-indole-4-carboxylate Property

Melting point:

53 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))

Boiling point:

320.2±15.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light yellow to yellow Crystal

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

Methyl 1-Methyl-1H-indole-4-carboxylate Chemical Properties,Usage,Production

Synthesis

To a 40 mL reaction vial was added a solution of methyl 1H-indole-4-carboxylate (400 mg, 2.28 mmol, 1.00 equiv) in N,N-dimethylformamide (10 mL). Sodium hydride (275 mg, 6.88 mmol, 3.00 equiv, 60% dispersed in mineral oil) was added in batches at 0 °C. After keeping stirring at 0 °C for 0.5 h, iodomethane (1.298 g, 9.14 mmol, 4.00 eq.) was slowly added dropwise at the same temperature. The reaction mixture was warmed to 25 °C and stirred for 15 hours. After completion of the reaction, the mixture was poured into ice water (50 mL) and extracted with ethyl acetate (50 mL x 3). The organic phases were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Methyl 1-methyl-4-indolecarboxylate (429 mg, 99%) was obtained as a red oil after concentration under reduced pressure. Mass spectrum (electrospray ionization, m/z): [M+H]+ 190.

References

[1] Patent: WO2017/205296, 2017, A1. Location in patent: Paragraph 78
[2] Patent: US2009/298809, 2009, A1. Location in patent: Page/Page column 17
[3] Heterocycles, 2006, vol. 67, # 2, p. 643 - 653