Indole-7-carboxaldehyde

Chemical Properties

Yellow Crystalline Solid

Uses

Indole-7-carboxaldehyde (cas# 1074-88-0) is a compound useful in organic synthesis.

Uses

Indole-7-carboxaldehyde is used in an efficient synthesis of fused pyrroloquinolinedicarboxylates from acetylenedicarboxylates and triphenylphosphine. 1.reactant for preparation of antiandrogens. 2.reactant for preparation of antiplatelet agent. 3.reactant for preparation of liver

Definition

ChEBI: Indole-7-carboxaldehyde is a member of indoles.

Synthesis Reference(s)

Synthetic Communications, 36, p. 1051, 2006 DOI: 10.1080/00397910500503470

Synthesis

General procedure for the synthesis of indole-7-carboxaldehyde from (1H-indol-7-yl)methanol: (1H-indol-7-yl)methanol (8.0 g, 54.3 mmol) was dissolved in 400 mL of dichloromethane, and activated manganese(IV) oxide (85%, 41.0 g, 0.40 mol) was added. The reaction mixture was stirred at room temperature for 72 hours. Upon completion of the reaction, 200 mL of dichloromethane and 400 mL of methanol were added to the mixture, followed by filtration through a silica gel pad to remove solid impurities. The filtrate was concentrated to give the crude product, which was further purified by silica gel column chromatography to afford the target product 1H-indole-7-carboxaldehyde (I-1) (6.55 g, 83% yield). The structure of the product was confirmed by 1H-NMR (CDCl3).

References

[1] Synthetic Communications, 2006, vol. 36, # 8, p. 1051 - 1056
[2] Patent: US2006/79520, 2006, A1. Location in patent: Page/Page column 43
[3] Patent: WO2006/44415, 2006, A2. Location in patent: Page/Page column 78; 106-107
[4] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4023 - 4034
[5] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4116 - 4125