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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1271233Generated: October 25, 2026

Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate → 2-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl Ester

https://huagongshe.com/reaction/1271233

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylateHCID 2773516—
Reactant4-Chloro-5,6,7,8-tetrahydroquinazolineHCID 12582969—
ReactantSodium t-butoxideHCID 23676156—
Product2-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl EsterHCID 136351946—

Reaction Steps

The title compound was synthesized according to the procedure described for Example 9 using sodium tert-butoxide (48 mg, 0.5 mmol), methyl 2-oxo-5-indolinecarboxylate (21 mg, 0.11 mmol) and 4-chloro-5,6,7,8-tetrahydroquinazoline solution (0.1 mL, 1 M in N-methylpyrrolidinone, corresponding to 17 mg, 0.1 mmol; described in: Budesinsky Z., Roubinek F. Collect. Czech. Chem. Commun., 1964, 29, 2341). The crude oil was purified on SCX-column pre-rinsed with methanol using ethyl acetate, methylene chloride, methylene chloride/methanol 1:1, and methanol/ammonia (2 M, aq) as elution solvents.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07205314B2
Source datasetuspto-grants-2007_04
ORD IDord-6f53902b6e3e48fda8c0489b0321e917
Source noteuspto-grants-2007_04