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

HRID 2178978Notes

Reaction equation

HRID 2178978 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-afeb75d11e9e48c9aced30f8e5f27e3c
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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