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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1821085Generated: October 31, 2026

Cyclohexanone → 6,9-Dichloro-1,2,3,4-tetrahydroacridine

https://huagongshe.com/reaction/1821085

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexanoneHCID 7967—
ReactantPhosphorus oxychlorideHCID 24813—
Reactant2-Amino-4-chlorobenzoic acidHCID 66646—
Product6,9-Dichloro-1,2,3,4-tetrahydroacridineHCID 21966498.2%

Reaction Steps

To a mixture of 2-amino-4-chlorobenzoic acid (4.5 g, 26.23 mmol) and cyclohexanone (2.72 mL, 26.23 mmoL) was added 22 mL phosphorus oxychloride. The mixture was heated to reflux for 3 hours. The excess phosphorus oxychloride was distilled off and the resulting mixture was treated with saturated sodium bicarbonate. The light brown precipitate was filtered, rinsed with water and dried under vacuum to give the desired product 6.50 g (25.77 mmoL, 98.2%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07605265B2
Source datasetuspto-grants-2009_10
ORD IDord-d7a238f84fac403183eb85f47fecef7d
Source noteuspto-grants-2009_10