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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2220746Generated: October 31, 2026

Methyl iodide → HCID 59773514, compound

https://huagongshe.com/reaction/2220746

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantAmmonium ChlorideHCID 25517—
Reactant3,4-dihydro-1H-pyrido[3,2-b]azepin-2(5H)-oneHCID 12283032—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
ProductHCID 59773514HCID 59773514—

Reaction Conditions

Temperature0 °C

Reaction Steps

A solution of 1.0 eq of 96 in 30 mL of dry THF was cooled to −78° C. While stirring, 1.1 eq of n-BuLi (2.5 M in hexanes) was added dropwise. The reaction solution was warmed to 0° C. and stirred for 1 hr. The solution was then cooled to −78° C. and 1.2 eq of methyl iodide was slowly added. The mixture was stirred, as the solution warmed to rt. After 17 hrs, 50 mL of saturated NH4Cl was added and extracted with EtOAc (3×50 mL). The combined organic extracts were dried over MgSO4 and vacuum filtered. The filtrate was rotary evaporated and dried under vacuum to afford a dark orange colored solid as 97.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07417152B2
Source datasetuspto-grants-2008_08
ORD IDord-ed2fb03b0ca143c6b1f69e97269dd8fb
Source noteuspto-grants-2008_08