8-Hydroxyquinoline → HCID 3265071, compound

HRID 541021Notes

Reaction equation

HRID 541021 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=1.[OH:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2>CC#N.O>[CH3:20][C:16]1[N:15]=[C:14]([NH:13][CH:7]([C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[C:23]2[C:22]([OH:21])=[C:31]3[C:26]([CH:27]=[CH:28][CH:29]=[N:30]3)=[CH:25][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 157652-Amino-6-methylpyridineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 3265071HCID 3265071, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared by both method A and method B presented for the compound of Example 1 with the change that 4-trifluoromethyl benzaldehyde (Sigma), 2-amino-6-picoline and 8-hydroxy-quinoline were used as starting materials. Product obtained (method B): C23H18F3N3O (MW: 409.1); 229 mg, 32.5%); m.p.: 136-138° C.; HPLC (CH3CN/H2O 70:30 Phenomenex C18 254 nm): Tr=10.18 min.

Workup

  1. customProduct obtained (method B)
  2. customTr=10.18 min.

Sources & evidence

ORD record
ord-c49ab89b7ed24a0cbfddc39243329943
Source dataset
uspto-grants-2014_10
Patent number
US08871937B2

Reaction notes

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