3-Methyl-2,4-pentanedione → HCID 178424484, compound

HRID 1813923Notes

Reaction equation

HRID 1813923 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].C[CH:18]([C:22](=O)[CH3:23])[C:19](=[O:21])C>>[CH3:23][C:22]1[CH:18]=[C:19]([OH:21])[C:12]2[C:11](=[C:10]([C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[CH:15]=[CH:14][CH:13]=2)[N:16]=1

Participants

3

Reactant 2

HCID 699493-Methyl-2,4-pentanedioneHCID 137578442-(2,4,6-Trimethylphenyl)aniline

Product 1

HCID 178424484HCID 178424484, compound

Conditions

Temperature
170 °C

Procedure

A mixture of 2′,4′,6′-trimethyl-biphenyl-2-ylamine(607 mg, 2.88 mmol) and methyl acetylacetone (607 mg, 5.75 mmol) in polyphosphoric acid (3 ml) was heated in 170° C. oil bath for 2.5 hours. The mixture was quenched with water and extracted twice with chloroform. The organic layer was washed with brine, dried and concentrated to give the title compound as an oil. The oil was pumped in vacuo, then trituated with a mixture of ether and hexane to give 642 mg (81%) of the title compound as a beige solid. The solid was recrystallized from ethyl acetate to give a beige solid, mp>250° C.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted twice with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5babae7267c4e94846f1761de8ceb10
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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