N,N-Diethylethylenediamine → HCID 13646090, compound

HRID 979494Notes

Reaction equation

HRID 979494 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH:12][C:13]1[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:15]([OH:17])=O)=O.[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][NH2:27])[CH3:23]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:27]([CH2:26][CH2:25][N:24]([CH2:28][CH3:29])[CH2:22][CH3:23])[C:15](=[O:17])[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 759761HCID 759761, compound

Product 1

HCID 13646090HCID 13646090, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.0 g (10 mmol) of methyl ester of N-(2-methoxyphenyl-acetyl)-anthranilic acid and 5.1 g (50 mmol) of 2-diethylaminoethylamine in ethanol (20 ml) was heated at 180° C. for 7 hours in a seald tube. After cooling, the thus obtained reaction mixture was purified by silica gel column chromatography (eluent; chloroform : ethanol=98:2) to obtain 1.24 g (yield 34 %) of 2-(2-methoxyphenylmethyl)-3-(2-diethylaminoethyl)-4(3H)-quinazolinone as an oily substance. 1.2 g of the oily substance were dissolved in ethanol (5 ml) and a 7% HCl-ethanol solution (1.5 ml) were added thereto. The resulting solution was allowed to cool overnight. The resulting colorless precipitates were collected by filtration to obtain 1.0 g of the captioned hydrochloride which is the desired compound.

Workup

  1. temperatureAfter cooling
  2. customthe thus obtained reaction mixture
  3. customwas purified by silica gel column chromatography (eluent; chloroform : ethanol=98:2)

Sources & evidence

ORD record
ord-4984c2b1cfd84dccba403b4228bf82ab
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

Loading…