Hydrochloric Acid → N-(cyanomethyl)-8-hydroxy-7-quinolinecarboxamide

HRID 2301445Notes

Reaction equation

HRID 2301445 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:18].Cl.CCN=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][NH:18][C:12]([C:3]1[C:2]([OH:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)=[O:14])#[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 18372631N-(cyanomethyl)-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. After approximately 30 minutes, a solid is collected and dried. The desired product is recrystallized from ethyl acetate (0.12 g).

Workup

  1. stirringstirred
  2. waitAfter approximately 30 minutes
  3. customa solid is collected
  4. customdried
  5. customThe desired product is recrystallized from ethyl acetate (0.12 g)

Sources & evidence

ORD record
ord-ed8d86046459469497aaf4d26053d0a1
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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