1-Hydroxybenzotriazole → HCID 19592861, compound

HRID 613577Notes

Reaction equation

HRID 613577 reaction equation
[NH:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][C:14]([Br:18])=[CH:13]2)C1C=CC=CC=1.[CH3:19][O:20][C:21]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=O)=[O:22].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Br:18][C:14]1[CH:15]=[N:16][C:17]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[NH:1][C:26](=[O:28])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([C:21]([O:20][CH3:19])=[O:22])[CH:24]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86754991HCID 86754991, compound

Product 1

HCID 19592861HCID 19592861, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-amiino-3-bromoquinoline (330 mg), 3-methoxycarbonylbenzoic acid (267 mg), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (369 mg) and 1-hydroxybenzotriazole (300 mg) in dimethylformamide (5 ml) was stirred at ambient temperature overnight. To the mixture was added water, and the resulting precipitates were collected by filtration, washed with hot methanol and dried to give 3-bromo-8-[3-(methoxycarbonyl)benzoylamino]quinoline (390 mg) as pale yellow solid.

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with hot methanol
  4. customdried

Sources & evidence

ORD record
ord-a455fec9d6634f4ab508f4e144778791
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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