2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 86736310, compound

HRID 904014Notes

Reaction equation

HRID 904014 reaction equation
[N:1]1([CH:10]([C:14]([OH:16])=[O:15])[C:11]([OH:13])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:17][CH:18]1[C:25](=[O:26])[N:24]2[CH:19]1[S:20][CH2:21][C:22]([CH3:34])=[C:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[CH2:35](OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)[CH3:36]>C(Cl)(Cl)Cl>[C:14]([CH:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:11]([NH:17][CH:18]1[C:25](=[O:26])[N:24]2[CH:19]1[S:20][CH2:21][C:22]([CH3:34])=[C:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:13])([O:16][CH2:35][CH3:36])=[O:15]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 12783021HCID 12783021, compoundHCID 23335811HCID 23335811, compound

Product 1

HCID 86736310HCID 86736310, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The monoethyl ester of 1H-indol-1-ylmalonic acid (3.96 mmole), (3.96 mmole) of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester and (3.96 mmole) of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) are mixed in 50 ml of hydrocarbon stabilized chloroform. The mixture is stirred overnight at room temperature under a nitrogen atmosphere. The reaction mixture is diluted with chloroform, washed with dilute aqueous hydrochloric acid, dilute aqueous sodium bicarbonate and water. The chloroform solution is dried over magnesium sulfate, filtered and evaporated to dryness to give the title compound.

Workup

  1. washwashed with dilute aqueous hydrochloric acid, dilute aqueous sodium bicarbonate and water
  2. dry with materialThe chloroform solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b90b5bb2850047508f6188a957eccd7e
Source dataset
uspto-grants-1980_10
Patent number
US04229574

Reaction notes

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