Morpholine → 2-(1-Naphthylmethylene)-3-(morpholinocarbonyl)propionic acid

HRID 986356Notes

Reaction equation

HRID 986356 reaction equation
[C:1]1([CH:11]=[C:12]2[CH2:17][C:16](=[O:18])[O:15][C:13]2=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>ClCCl>[C:1]1([CH:11]=[C:12]([CH2:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 543164283-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dione

Product 1

HCID 545343202-(1-Naphthylmethylene)-3-(morpholinocarbonyl)propionic acidYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 1.00 g of the 2-(1-naphthylmethylene)succinic anhydride and 0.37 g of morpholine in 31 ml of dry dichloromethane was stirred for 2 hours at room temperature. The reaction mixture was evaporated under reduced pressure, and the residue was triturated with a mixture of ethyl acetate, benzene and hexane (1/1/1 by volume) to obtain 1.10 g of 2-(1-naphthylmethylene)-3-(morpholinocarbonyl)propionic acid as colorless crystals.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue was triturated with a mixture of ethyl acetate, benzene and hexane (1/1/1 by volume)

Sources & evidence

ORD record
ord-ccc411c7493c40708ea7fc821954fb5d
Source dataset
uspto-grants-1987_12
Patent number
US04711958

Reaction notes

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