4-Fluorobenzoyl chloride → 2-[(2-Methyl-4-(4-fluorobenzamido)phenyl)amino]-1-pyrroline, hydrochloride

HRID 484794Notes

Reaction equation

HRID 484794 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([Cl:24])=[O:23])=[CH:20][CH:19]=1>C(#N)C.C(OCC)C>[ClH:24].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([F:17])=[CH:19][CH:20]=2)[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Product 1

HCID 704656942-[(2-Methyl-4-(4-fluorobenzamido)phenyl)amino]-1-pyrroline, hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.0 g (3.8 mmole) of product compound of Example 9 and 30.5 mmole of p-fluorobenzoyl chloride in 40 ml of acetonitrile was stirred at reflux for four hours, after which time thin-layer chromatography on silica gel (9:1 ethanol/concentrated aqueous ammonia) indicated no unreacted starting amine. The reaction mixture was then diluted eight-fold with diethyl ether. The resultant solid was collected and washed with three portions of ether, then dried in a high vacuum over 5A molecular sieves, giving the title compound as the hydrochloride salt. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. temperatureat reflux for four hours
  2. customThe resultant solid was collected
  3. washwashed with three portions of ether
  4. dry with materialdried in a high vacuum over 5A molecular sieves

Sources & evidence

ORD record
ord-6aa09732f1ee488fa71abb5963290fc5
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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