Sodium Azide → ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate

https://huagongshe.com/reaction/519366

Participants

Role	Name	HCID	Charge
Reactant	Sodium Azide	HCID 33557	—
Reactant	Ethyl 3-(2-chlorocyclohex-1-enyl)acrylate	HCID 57360807	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate	HCID 300702	93.3%

Reaction Conditions

Temperature	105 °C

Reaction Steps

To a mixture of ethyl 3-(2-chlorocyclohex-1-enyl)acrylate (21.4 g, 100 mmol) in DMSO (100 mL) was added sodium azide (9.75 g, 150 mmol). The reaction mixture was heated at 105° C. for 4 h. After cooling to room temperature, the mixture was poured into ice water. The resulting precipitate was collected by filtration to afford 121a (18.0 g, 93.3%). MS-ESI: [M+H]+ 194.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115152B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-79a63a4d650948a99e4cc0ed9d2800b5
Source note	uspto-grants-2015_08