Acetyl chloride → 2-[(2-Methyl-4-acetamidopheny)amino]-1-pyrroline, hydrochloride

HRID 484791Notes

Reaction equation

HRID 484791 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.[C:17]([Cl:20])(=[O:19])[CH3:18]>C(#N)C.C(OCC)C>[ClH:20].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:17](=[O:19])[CH3:18])[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 6367Acetyl chlorideHCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Product 1

HCID 704665062-[(2-Methyl-4-acetamidopheny)amino]-1-pyrroline, hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.0 g (3.8 mmole) of the product compound of Example 9 and 30.5 mmole of acetyl chloride in 40 ml of acetonitrile was stirred at room temperature for 18 to 20 hours. 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. customThe resultant solid was collected
  2. washwashed with three portions of ether
  3. dry with materialdried in a high vacuum over 5A molecular sieves

Sources & evidence

ORD record
ord-f8764537e48d4342b4ed5d8d24f13e49
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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