Sodium Hydroxide → HCID 178489902, compound

HRID 1508548Notes

Reaction equation

HRID 1508548 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:12])=O)=[CH:5][CH:4]=1.COC(OC)[N:16]([CH3:18])C.O.[NH2:22]N.[OH-].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[N:12]=[CH:18][NH:16][N:22]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 2418682-(4-Methoxyphenyl)acetamide

Product 1

HCID 178489902HCID 178489902, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(4-methoxyphenyl)acetamide (1.51 g, 9.14 mmol) and N,N-dimethylformamide dimethyl acetal (6 ml, 45.0 mmol) in a r.b.f, equipped with a Dean-Stark trap was placed in a 120° C. bath (turned to solution once heated) for 1.5 hours. The reaction was cooled and concentrated, then, added AcOH (18 ml), hydrazine hydrate (0.611 ml, 10.06 mmol), and heated at 90° C. for 1.5 hours. After cooling to RT, added 2M aqueous sodium hydroxide and extracted 3 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with MeOH in DCM to afford the title compound. Mass spectrum (ESI) 190.3 (M+1).

Workup

  1. customequipped with a Dean-Stark trap
  2. customwas placed in a 120° C.
  3. temperatureonce heated) for 1.5 hours
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated
  6. temperatureAfter cooling to RT
  7. extractionextracted 3 times with ethyl acetate
  8. washThe combined organics were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by flash column chromatography on silica gel
  13. washeluting with MeOH in DCM

Sources & evidence

ORD record
ord-69a8d72d0a1e46c0a07cfe93eb821612
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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