8-Hydroxyquinoline → HCID 54673787, compound

HRID 541026Notes

Reaction equation

HRID 541026 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[O:16].O[C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][CH:24]=[CH:23]2>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH:18]([C:27]2[CH:22]=[CH:23][CH:24]=[CH:25][N:26]=2)[C:19]2[C:15]([OH:16])=[C:10]3[C:11]([CH:12]=[CH:13][CH:14]=[N:9]3)=[CH:21][CH:20]=2)=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 19238-HydroxyquinolineHCID 142732-PyridinecarboxaldehydeHCID 661742-Amino-5-chloropyridine

Product 1

HCID 54673787HCID 54673787, compound

Conditions

Temperature
60 °C

Procedure

The title compound was prepared by method B presented for the compound of Example 1; 2-amino-5-chloro-pyridine, 2-pyridine-carboxaldehyde and 8-hydroxy-quinoline were used in the reaction; the reaction mixture was heated at 60° C. for 3 days. Greyish-white powder, product purified by column chromatography. C20H18ClN4O; (MW: 362.1); yield: 55 mg, (23.7%). m.p.: 160-162° C., HPLC (CH3CN/H2O 70:30 Phenomenex C18 282 nm): 5.69 min.

Workup

  1. customGreyish-white powder, product purified by column chromatography
  2. custom5.69 min.

Sources & evidence

ORD record
ord-3167a8fac52b4526be95bc99c97a987b
Source dataset
uspto-grants-2014_10
Patent number
US08871937B2

Reaction notes

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