1,2-Dichloroethane → N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide

HRID 25779Notes

Reaction equation

HRID 25779 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:15]([OH:23])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:24][CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[CH:34]=2)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=1.C(N(C(C)C)CC)(C)C>CCOC(C)=O.C(Cl)Cl>[CH3:43][O:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=[C:26]2[CH2:25][NH:24][C:15](=[O:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22566510HCID 22566510, compound

Product 1

HCID 10408574N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamideYield 22.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round bottom flask equipped with a stir bar was charged with EDC (0.224 mmol, 1.1 equiv), HOBT (0.224 mmol, 1.1 equiv), benzoic acid (0.224 mmol, 1.1 equiv), 4-aminomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (0.204 mmol, 1 equiv) and 3.3 mL of methylene chloride. Diisopropyl ethyl amine (0.224 mmol, 1.1 equiv) was added last, the reaction was placed under argon, and stirred at room temperature overnight. The crude reaction mixture was transferred to a separatory funnel, diluted with EtOAc, and washed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine. The organics were concentrated in vacuo to afford a brown oil. The product was purified by column chromatography using silica gel eluting with a gradient of 10-50% EtOAc/hexanes. The product fractions were pooled and concentrated in vacuo to afford 18 mg of the title compound as a yellow oil.

Workup

  1. customA round bottom flask equipped with a stir bar
  2. customThe crude reaction mixture
  3. customwas transferred to a separatory funnel
  4. washwashed with 1 N HCl, aqueous saturated sodium bicarbonate (NaHCO3) solution, and brine
  5. concentrationThe organics were concentrated in vacuo
  6. customto afford a brown oil
  7. customThe product was purified by column chromatography
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e427c06399c41cbb4bb5db02dd0b691
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

Loading…