2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 14372047, compound

HRID 1382694Notes

Reaction equation

HRID 1382694 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](=[N:28][NH2:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)Cl>[C:16]1([C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:28][NH:29][C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 79304DiphenylmethylidenehydrazineHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 14372047HCID 14372047, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20.0 g (0.10 mole) of t-butyloxycarbonyl-L-serine, 19.6 g (0.10 mole) of benzophenone hydrazone, and 24.7 g of 2-ethoxy-1(2H)-quinolinecarboxylic acid ethyl ester in 250 ml of methylene chloride was stirred at room temperature for 16 hours. The solution was extracted with successive 100 ml portions of 1N hydrochloric acid, water, saturated sodium bicarbonate solution, water and brine, then dried over magnesium sulfate. The solvent was evaporated in vacuo and the resulting syrup was dissolved in ethyl acetate and crystallized by the addition of hexane to afford 24.5 g (64%) of product, mp 150.0°-152.5° C.

Workup

  1. extractionThe solution was extracted with successive 100 ml portions of 1N hydrochloric acid, water, saturated sodium bicarbonate solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe resulting syrup was dissolved in ethyl acetate
  5. customcrystallized by the addition of hexane

Sources & evidence

ORD record
ord-7c00ce62055041c6902b74da40b7ab82
Source dataset
uspto-grants-1989_02
Patent number
US04808579

Reaction notes

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