Dimethylamine, hydrochloride → HCID 19592732, compound

HRID 613579Notes

Reaction equation

HRID 613579 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=O)[CH:15]=1.Cl.[CH3:25][NH:26][CH3:27].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:22])[N:26]([CH3:27])[CH3:25])[CH:15]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 19592340HCID 19592340, compound

Product 1

HCID 19592732HCID 19592732, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-8-(3-carboxybenzoylamino)quinoline (200 mg), dimethylamine hydrochloride (65.9 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (100 mg) and 1-hydroxybenzotriazole (109 mg) in dimethylformamide (3 ml) was stirred for 3 hours at ambient temperature. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (ethyl acetate) and recrystallized from ethanol to give 3-bromo-8-[3-(dimethylcarbamoyl)benzoylamino]quinoline (120 mg) as pale yellow solid.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (ethyl acetate)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4be17155f97c4865b80c444c99a1c3b9
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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