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

HRID 441249

Reaction equation

HRID 441249 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:20]12[C:27]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:26]3[C:25](=[O:32])[O:24][C:22](=[O:23])[C:21]1=[CH:33][CH:34]=[CH:35][CH:36]=2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:22]([C:21]1[CH:33]=[CH:34][CH:35]=[CH:36][C:20]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]([NH: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)=[O:32])([OH:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 72794Diphenic anhydrideHCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

Product 1

HCID 224051021-{4-[2-(2-Carboxyphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinolineYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (252 mg), diphenic anhydride (224 mg), triethylamine (202 mg) and catalytic amount of 4-dimethylaminopyridine in dichloromethane (15 ml) was stirred for 8 hours at ambient temperature. The mixture was evaporated in vacuo and diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate aqueous solution, brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and triturated from ethyl acetate to give 1-{4-[2-(2-carboxyphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (400 mg).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate aqueous solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customtriturated from ethyl acetate

Sources & evidence

ORD record
ord-0cfb53e26d7849009cbdc96b6092b079
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Linked notes

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