Methacrylic Acid → 8-(2,6-Dichlorobenzoylamino)-4-(2-methacryloylhydrazino)quinoline

HRID 613549Notes

Reaction equation

HRID 613549 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH2:18])=[O:5].[C:24](O)(=[O:28])[C:25]([CH3:27])=[CH2:26].ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26])=[O:5]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 757711-HydroxybenzotriazoleHCID 19592850HCID 19592850, compound

Product 1

HCID 195923738-(2,6-Dichlorobenzoylamino)-4-(2-methacryloylhydrazino)quinolineYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-4-hydrazinoquinoline (200 mg), methacrylic acid (54.5 mg), 1-ethyl-3-(3-dimethylaminopropyl)-arbodiimide hydrochloride (133 mg) and 1-hydroxybenzotriazole (93.4 mg) in dimethylformamide (4 ml) was stirred for 4.5 hours at ambient temperature. The mixture was diluted with ethyl acetate and washed with water, saturated sodium bicarbonate solution and brine. The insoluble materials were collected by filtration and recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-(2-methacryloylhydrazino)quinoline (190 mg).

Workup

  1. washwashed with water, saturated sodium bicarbonate solution and brine
  2. filtrationThe insoluble materials were collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-19c50daefb4f464eb0ab9ba740ab7ccb
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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