2,4-Dimethylacetophenone → HCID 4418957, compound

HRID 868746Notes

Reaction equation

HRID 868746 reaction equation
O.[C:2]([OH:6])(=O)[CH:3]=O.[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[C:15](=O)[CH3:16].[NH4+:18].[OH-].[NH2:20]N>O>[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:16]=[CH:3][C:2](=[O:6])[NH:18][N:20]=1

Participants

6

Reactant 4

HCID 69852,4-DimethylacetophenoneHCID 9321HydrazineHCID 14923Ammonium HydroxideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 4418957HCID 4418957, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of glyoxylic acid monohydrate (920 mg, 10 mmol) and 2′,4′-dimethylacetophenone (4.45 mL, 30 mmol) was stirred at 150° C. for 2 hr. Then the mixture was cooled down to room temperature and water (4 mL) was added followed by conc. aq. NH4OH (1 mL). The mixture was washed with DCM. To the ammoniac solution was added hydrazine (314 μL, 10 mmol) and the solution was refluxed for 3 hours. After cooling to room temperature the precipitate was collected by filtration to give the desired product as a white powder (1.1 g, 55%), 1H NMR (300 MHz, dMSO): δ 2.22 (s, 3H), 2.25 (s, 3H), 6.93-6.95 (d, 1H), 7.15 (m, 3H), 7.21-7.23 (d, 1H), 7.57-7.61 (d, 1H), 13.1 (bs, 1H); (M+H, 201).

Workup

  1. temperatureThen the mixture was cooled down to room temperature
  2. washThe mixture was washed with DCM
  3. temperaturethe solution was refluxed for 3 hours
  4. temperatureAfter cooling to room temperature the precipitate
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-75de85d93fe34b828130e8c7813a83ee
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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