1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178487892, compound

HRID 526258Notes

Reaction equation

HRID 526258 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31]([NH:34][CH:35]=[C:36]([C:42](=[O:46])[CH:43]([CH3:45])[CH3:44])[C:37]([O:39]CC)=O)=[CH:30][CH:29]=1>>[OH:39][C:37]1[C:32]2[C:31](=[CH:30][CH:29]=[C:28]([O:27][CH3:26])[N:33]=2)[N:34]=[CH:35][C:36]=1[C:42](=[O:46])[CH:43]([CH3:44])[CH3:45]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 178471949HCID 178471949, compound

Product 1

HCID 178487892HCID 178487892, compoundYield 141.6%

Procedure

To a flask containing Dowtherm™ A (400 mL) at 250° C. was added ethyl 2-(((6-methoxypyridin-3-yl)amino)methylene)-4-methyl-3-oxopentanoate (11.5 g, 39.3 mmol) portion wise over 3 to 5 min and the reaction mixture was stirred for an additional 30 to 45 min. The reaction mixture was removed from the heat source, cooled to room temperature and diluted with hexanes to facilitate precipitation. The solids were filtered, washed with hexanes and dried under vacuum to afford the desired product (13.7 g, crude) as a yellow-brown solid: ESI MS m/z 247 [M+H]+.

Workup

  1. customThe reaction mixture was removed from the heat source
  2. additiondiluted with hexanes
  3. customprecipitation
  4. filtrationThe solids were filtered
  5. washwashed with hexanes
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d26de7ae2cb84a599f1ad6d57764e878
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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