Ethylamine hydrochloride → 2-Methylquinoline

HRID 864602Notes

Reaction equation

HRID 864602 reaction equation
C(C1C=CC(C=CC(NCC(N(C2C(Cl)=C(C(Cl)=CC=2)CO[C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=2[N:31]=[C:30]([CH3:33])[CH:29]=[CH:28]3)C)=O)=O)=CC=1)(O)=O.Cl.C(N)C.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O>[CH3:33][C:30]1[CH:29]=[CH:28][C:27]2[C:32](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:31]=1

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54355870HCID 54355870, compound

Product 1

HCID 70602-MethylquinolineYield 367.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-[3-[N-(4-carboxycinnamoylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (100 mg), ethylamine hydrochloride (16.9 mg) and N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (32.2 mg) and 1-hydroxybenzotriazole (30.4 mg), and the mixture was stirred for 6 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (methylene chloride-methanol) to give 8-[2,6-dichloro-3-N-[4-(ethylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylquinoline (91 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (methylene chloride-methanol)

Sources & evidence

ORD record
ord-dd42da7a821c48888a0c6e82c7adbcce
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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