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

HRID 2050378Notes

Reaction equation

HRID 2050378 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-c08c3f9466d1445d9344dea37576ea55
Source dataset
uspto-grants-1980_04
Patent number
US04200747

Reaction notes

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