Hydrochloric Acid → Cyanomethyl-8-hydroxy-7-quinolinecarboxamide

HRID 382895Notes

Reaction equation

HRID 382895 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.[NH2:15][CH2:16][C:17]#N.Cl.CC[N:22]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O.C(N(CC)CC)C>[C:16]([CH2:17][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[C:3]([C:12]([NH2:22])=[O:14])=[CH:4][CH:5]=2)[N:10]=1)#[N:15]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10901AminoacetonitrileHCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86757553Cyanomethyl-8-hydroxy-7-quinolinecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

8-hydroxyquinoline-7-carboxylic acid (0.51 g), aminoacetonitrile.HCl (0.27 g), and triethylamine (0.38 mL) are dissolved in 10 mL dimethylformamide. EDC.HCl (0.54 g) and HOBt.H2O (0.38 g) are added and the reaction is stirred at room temperature for 2 days. The reaction is poured into 50 mL ice/H2O and stirred.

Workup

  1. stirringstirred

Sources & evidence

ORD record
ord-a3ecd77c8a594a2393fb04309cc1f8e3
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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