2-Pyridinecarboxaldehyde → 7-Iodo-1-pyridin-2-yl-[1,2,4]triazolo[4,3-a]quinoline

HRID 2075691Notes

Reaction equation

HRID 2075691 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][NH2:13])[CH:6]=[CH:5]2.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=3)=[N:13][N:12]=[C:7]1[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 12217721Iodo benzene diacetateHCID 53403040(6-Iodo-quinolin-2-yl)-hydrazine

Product 1

HCID 670909637-Iodo-1-pyridin-2-yl-[1,2,4]triazolo[4,3-a]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (6-Iodo-quinolin-2-yl)-hydrazine (2.99 g, 10.5 mmol) suspended in CH2Cl2 (30 mL) was added 2-pyridinecarboxaldehyde (1.2 mL, 12.6 mmol). The reaction was stirred at room temperature for 2 hours, followed by the addition of iodobenzene diacetate (3.39 g, 10.5 mmol). The reaction was stirred overnight at room temperature, during which time a precipitate formed. The mixture was concentrated to half the volume, and the precipitate was filtered and washed with minimal CH2Cl2 to give the desired product, 5k. The filtrate was concentrated and suspended in EtOH. After stirring overnight at room temperature, the mixture was filtered and rinsed with EtOH to obtain additional product, 5k.

Workup

  1. stirringThe reaction was stirred overnight at room temperature, during which time a precipitate
  2. customformed
  3. concentrationThe mixture was concentrated to half the volume
  4. filtrationthe precipitate was filtered
  5. washwashed with minimal CH2Cl2

Sources & evidence

ORD record
ord-0de7e5fe627a46139bccc5c89a4503f6
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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