Diisopropylethylamine → 8-Hydroxy-N-[(4-nitrophenyl)methyl]-7-quinolinecarboxamide

HRID 1069510Notes

Reaction equation

HRID 1069510 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl.[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>O.CN(C=O)C>[OH:1][C:2]1[C:3]([C:12]([NH:24][CH2:23][C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:26][CH:25]=2)=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 183726868-Hydroxy-N-[(4-nitrophenyl)methyl]-7-quinolinecarboxamideYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Hydroxyquinoline-7-carboxylic acid (0.51 g) of Preparation 1 is added to 20 mL DMF. 4-Nitrobenzylamine hydrochloride (0.53 g) followed by diisopropylethylamine (0.49 mL) is then added. After 10 minutes, all solids go into solution. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.54 g) and 1-hydroxybenzotriazole monohydrate (0.38 g) are added and the reaction stirred at room temperature overnight. The reaction is poured into 75 mL H2O. The resulting solid is filtered and dried to give the title product (0.53 g).

Workup

  1. additionis then added
  2. filtrationThe resulting solid is filtered
  3. customdried

Sources & evidence

ORD record
ord-e3784cb7c33f4846a811d0a3560b478f
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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