1-Hydroxybenzotriazole → N-(cyanomethyl)-8-hydroxy-7-quinolinecarboxamide

HRID 323010Notes

Reaction equation

HRID 323010 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.[NH2:16][CH2:17][C:18]#[N:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O.C(N(CC)CC)C>[C:17]([CH2:18][NH:19][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:16]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11491918Aminoacetonitrile hydrochloride

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-3159ff09aeba41b6a4e0083412f3a63c
Source dataset
uspto-grants-2001_04
Patent number
US06211376B1

Reaction notes

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