Ethanol → HCID 3002907, compound

HRID 577434Notes

Reaction equation

HRID 577434 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-:12].[K+].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:21](O)[CH3:22]>>[CH:14]1([C:21]2[CH:22]=[C:4]([C:2]([OH:12])=[O:3])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:1]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 702EthanolHCID 7054IsatinHCID 7967CyclohexanoneHCID 14797Potassium Hydroxide

Product 1

HCID 3002907HCID 3002907, compound

Procedure

A mixture of 2.94 g (0.02 mole) isatine and 50 ml ethanol and 2.24 g (0.04 mole) potassium hydroxide and 2 g (0.02 mole) cyclohexanone is refluxed to give cyclohexylquinoline-4-carboxylic acid. This acid is dried and dissolved in 50 ml THF and 2 ml ethylchloroformate and 2 ml three ethylamine are added over an ice bath. After 3 hrs stirring 3.9 g (0.02 mole) 4-aminophenoxyisobutyric acid is added and stirring continued for 4 hrs. After filtration most of THF is evaporated and diluted with water and acidified with hydrochloric acid to get the final compound. The structure is structure 18. C29H20N2O4 mw 400 If other cyclic ketones such as cycloheptanone are used the corresponding cycloheptyl compound is obtained.

Workup

  1. temperatureis refluxed

Sources & evidence

ORD record
ord-b92b101668aa482289401381f70c4a0a
Source dataset
uspto-grants-2015_05
Patent number
US09040553B2

Reaction notes

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