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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2228349Generated: October 27, 2026

Benzoic Acid → 2-cyano-2-(5,6-dimethoxy-3,3-dimethyl-indan-1-ylidene)-N-prop-2-ynyl-acetamide

https://huagongshe.com/reaction/2228349

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic AcidHCID 243—
ReactantPyrrolidineHCID 31268—
Reactant2-cyano-N-(prop-2-yn-1-yl)acetamideHCID 18469579—
ReactantCyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl EsterHCID 54568492—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product2-cyano-2-(5,6-dimethoxy-3,3-dimethyl-indan-1-ylidene)-N-prop-2-ynyl-acetamideHCID 5376305449.9%

Reaction Steps

A 50 ml reaction flask equipped with a water separator and a reflux condenser was charged with 2.2 g of 2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (see Example 1), 1.2 g of 2-cyano-N-prop-2-ynyl-acetamide (see above), catalytic amounts of pyrrolidine, and benzoic acid in 20 ml of toluene. The reaction mixture was refluxed for 24 hours with simultaneous separation of water. Then, the product in the cold reaction mixture was filtered off and recrystallized in ethylacetate to yield 1.13 g of white crystals, m.p. 202° C.-205° C. UV 362 nm (ε=24′992). Solubility: 0.04% in CÉTIOL LC

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06416746B1
Source datasetuspto-grants-2002_07
ORD IDord-977eda4c26f94a08a72c5bb4fee4b043
Source noteuspto-grants-2002_07