8-Hydroxyquinoline → HCID 54673781, compound

HRID 541025Notes

Reaction equation

HRID 541025 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1.[OH:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[CH:27][CH:26]=[CH:25]2>>[CH3:18][C:14]1[N:13]=[C:12]([NH:11][CH:5]([C:4]2[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=2)[C:21]2[C:20]([OH:19])=[C:29]3[C:24]([CH:25]=[CH:26][CH:27]=[N:28]3)=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 19238-HydroxyquinolineHCID 157652-Amino-6-methylpyridineHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 54673781HCID 54673781, compound

Procedure

The title compound was prepared by method B presented for the compound of Example 1 with the change that 3,4-difluorobenzaldehyde was reacted with 2-amino-6-picoline and 8-hydroxy-quinoline. White powder precipitated, C22H17F2N3O, (MW: 377.1); yield; 275 mg (53.3%). m.p.: 162-165° C.; HPLC (CH3CN/H2O 70:30 Phenomenex C18 282 nm): 7.97 min.

Workup

  1. customWhite powder precipitated
  2. custom7.97 min.

Sources & evidence

ORD record
ord-374aab20d5a4453faf44dbb6f29fed12
Source dataset
uspto-grants-2014_10
Patent number
US08871937B2

Reaction notes

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