1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → 6-((4-Chlorophenyl)(thiazol-2-yl)methyl)quinolin-4-ol

HRID 1778283Notes

Reaction equation

HRID 1778283 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH:16]=[C:17]3C(=O)OC(C)(C)[O:19][C:18]3=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[C:9]2[CH:14]=[C:13]3[C:12](=[CH:11][CH:10]=2)[N:15]=[CH:16][CH:17]=[C:18]3[OH:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 1183240095-(((4-((4-Chlorophenyl)(thiazol-2-yl)methyl)phenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 1785163976-((4-Chlorophenyl)(thiazol-2-yl)methyl)quinolin-4-ol

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

5-(((4-((4-Chlorophenyl)(thiazol-2-yl)methyl)phenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.8 g, 3.957 mmol) was added as a solid portionwise over 3-4 minutes to DOWTHERM (75 mL) at 220° C. The resulting mixture was heated for 20 minutes, cooled to room temperature, and treated with excess heptane (30 mL) with stirring. After allowing the solid to settle, the supernatant was decanted and the process repeated 3 times. After concentrating to remove heptane, the residue was purified by MPLC using a dichloromethane-methanol gradient to yield 6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-4-ol. (ES, m/z) 352, 354 [M+H]+

Workup

  1. temperatureThe resulting mixture was heated for 20 minutes
  2. customthe supernatant was decanted
  3. concentrationAfter concentrating
  4. customto remove heptane
  5. customthe residue was purified by MPLC

Sources & evidence

ORD record
ord-41f68094ef9241fa823240a0e6c99e99
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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