Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2208767Generated: November 1, 2026

Acetic Acid → HCID 70873657, compound

https://huagongshe.com/reaction/2208767

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantTetrahydro-4H-pyran-4-oneHCID 121599—
ReactantSodium cyanoborohydrideHCID 5003444—
ReactantMethyl 3-amino-5-chloro-2-methylbenzoateHCID 68295455—
SolventMethanolHCID 887—
ProductHCID 70873657HCID 7087365735.5%

Reaction Steps

To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (1 g, 5.02 mmol) and tetrahydropyran-4-one (2.5 g, 25 mmol) in methanol (10 mL), acetic acid (0.3 g, 5.02 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.63 g, 10.05 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford methyl 5-chloro-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (0.5 g, 35.5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376422B2
Source datasetuspto-grants-2016_06
ORD IDord-9b1fceb76aa84b9fa96356cd53ac0411
Source noteuspto-grants-2016_06