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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 448155Generated: October 29, 2026

Dimethylformamide → 4-(Dibenzylamino)-6-methoxy-1-naphthaldehyde

https://huagongshe.com/reaction/448155

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPhosphorus oxychlorideHCID 24813—
ReactantN,N-dibenzyl-7-methoxynaphthalen-1-amineHCID 59813090—
Product4-(Dibenzylamino)-6-methoxy-1-naphthaldehydeHCID 59813117—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a stirred solution of DMF (30 mL) was added POCl3 (10.65 mL, 116 mmol) over 30 minutes at 0° C. The mixture was then stirred at 0° C. for 30 minutes and added 4 (11.75 g, 33.2 mmol) in DMF (120 mL). The mixture was stirred at room temperature for six days and the poured into ice-water. The product mixture was extracted with dichloromethane and the organic layer washed with water, aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated to afford 13.58 g of 4-(dibenzylamino)-6-methoxy-1-naphthaldehyde (5) which was used in next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08481581B2
Source datasetuspto-grants-2013_07
ORD IDord-fd087be93fa64e4c88e1eb9cc41befac
Source noteuspto-grants-2013_07