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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1253140Generated: November 1, 2026

Toluene → 3-(4-Dimethylamino-2-n-pentyloxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide

https://huagongshe.com/reaction/1253140

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantAcetic AnhydrideHCID 7918—
Reactant3-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-HCID 112344—
Reactant1-n-Pentyloxy-3-dimethylaminobenzeneHCID 20136807—
SolventMethanolHCID 887—
Product3-(4-Dimethylamino-2-n-pentyloxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalideHCID 1417772080.1%

Reaction Steps

Into 75 ml of acetic anhydride, 9.2 g of (1-ethyl-2-methylindol-3-yl) (3-carboxypyridin-2-yl) ketone and 7050 g of 1-n-pentyloxy-3-dimethylaminobenzene were added, and the resultant mixture was stirred for 4 hours at 60° to 65° C. After cooling the reaction mixture to room temperature, the cooled reaction mixture was poured into 500 ml of ice water and the resultant mixture was treated with toluene and methanol by the same manner as in Synthetic Example 1. As a result, 11.9 g of the objective compound were obtained as pale blue crystals (melting point: 169° to 171° C.). The elementary analytical data of the product were as follows.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04747875
Source datasetuspto-grants-1988_05
ORD IDord-0d99a088ec644612bf3d62b212567728
Source noteuspto-grants-1988_05