N,N-Dimethylaniline → 6-Acetamido-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653127Notes

Reaction equation

HRID 653127 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16](=[O:19])[CH2:17][CH3:18])[CH2:11][CH2:10][C:9]2=[O:20].CN(C)C1C=CC=CC=1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16](=[O:19])[CH2:17][CH3:18])[CH2:11][CH2:10][C:9]2=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 6367Acetyl chlorideHCID 212947846-Amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 212948106-Acetamido-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 90.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetyl chloride (0.604 g) in methylene chloride (5 ml) was added dropwise to a solution of 6-amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.526 g) and N,N-dimethylaniline (1.016 g) in methylene chloride (15 ml) with ice cooling over a period of 10 minutes and stirred for further 20 minutes. The mixture was diluted with chloroform, washed successively with 10% hydrochloric acid, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was recrystallized from methanol to give 6-acetamido-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.64 g).

Workup

  1. washwashed successively with 10% hydrochloric acid, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residual solid was recrystallized from methanol

Sources & evidence

ORD record
ord-7c5e8aef49b64a88908b11c4412df1c2
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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