Methanol → 1-{4-[2-(4-Methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

HRID 441241Notes

Reaction equation

HRID 441241 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N([CH2:25][CH3:26])CC)C.[CH3:27][OH:28]>ClCCl.C(Cl)(Cl)Cl>[CH3:6][C:5]1[CH:4]=[CH:3][C:2]([C:26]2[CH:25]=[CH:9][CH:10]=[CH:11][C:12]=2[C:27]([NH:1][C:2]2[CH:19]=[CH:18][C:5]([C:6]([N:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:11][CH2:10][CH2:9]3)=[O:7])=[CH:4][CH:3]=2)=[O:28])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

Product 1

HCID 105035441-{4-[2-(4-Methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methylphenyl)benzoic acid (140 mg) in dichloromethane (5 ml) were added oxalyl chloride (133 mg) and a few drop of N,N-dimethylformamide and the solution was stirred at ambient temperature for 2 hours. Dichloromethane was evaporated in vacuo to give an acid chloride as an oil and the oil was added to a mixture of 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (166 mg) and triethylamine (0.14 ml) in dichloromethane (20 ml). The mixture was stirred at ambient temperature for 2 hours, washed successively with diluted hydrogen chloride, water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give an oil and the oil was subjected to silica gel column (30 g, 1% methanol in chloroform) to give 1-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (202 mg) as an amorphous solid.

Workup

  1. washwashed successively with diluted hydrogen chloride, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-f4e7c6fdea184ac1af3418aa2524b819
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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