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

HRID 441242

Reaction equation

HRID 441242 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[NH2:32][C:33]1[CH:50]=[CH:49][C:36]([C:37]([N:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:42][CH2:41][CH2:40]2)=[O:38])=[CH:35][CH:34]=1.C(N(CC)CC)C>O1CCCC1>[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH:32][C:33]2[CH:50]=[CH:49][C:36]([C:37]([N:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42][CH2:41][CH2:40]3)=[O:38])=[CH:35][CH:34]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 7285212-(1H-pyrrol-1-yl)benzoic acidHCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

Product 1

HCID 105982751-{4-[2-(1-Pyrrolyl)benzoylamino]benzoyl}-1,2,3,4tetrahydroquinolineYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-pyrrolyl)benzoic acid (206 mg), diphenyl chlorophosphate (325 mg), 1-(4-aminobenzoyl}-1,2,3,4-tetrahydroquinoline (277 mg) in tetrahydrofuran (10 ml) was added triethylamine (333 mg) at 0° C. The resulting mixture was allowed to warm to ambient temperature where it was maintained for 5 hours. The solvent was evaporated and diluted with ethyl acetate and washed with water, saturated sodium bicarbonate aqueous solution and brine. The organic layer was dried over sodium sulfate and concentrated to give 1-{4-[2-(1-pyrrolyl)benzoylamino]benzoyl}-1,2,3,4tetrahydroquinoline (280 mg).

Workup

  1. temperaturewas maintained for 5 hours
  2. customThe solvent was evaporated
  3. additiondiluted with ethyl acetate
  4. washwashed with water, saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b85ecc7cd5d44739bc7c54ad7db59d8c
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Linked notes

Loading…