Formic Acid → HCID 23128157, compound

HRID 358684Notes

Reaction equation

HRID 358684 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[C:14]([NH:21][CH3:22])[CH:13]=1.[OH-].[Na+]>O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][C:14]=1[N:21]([CH3:22])[CH:8]=[O:10])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 45086270HCID 45086270, compound

Product 1

HCID 23128157HCID 23128157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (23.3 ml) and formic acid (15.9 ml) was stirred at 50 to 60° for 90 minutes and then cooled to 0 to 5° in an ice/salt bath. 4'-Methyl-2'-(methylamino)acetophenone (17.25 g) was added and the solution stirred at 20° for 3 hours. The reaction mixture was cooled to 0° and water (80 ml) added dropwise whilst maintaining the temperature below 8°. Aqueous sodium hydroxide (specific gravity 1.5, 60 ml) was added dropwise whilst maintaining the temperature below 10°. The mixture was extracted with dichloromethane (3×30 ml). The combined extracts were washed with aqueous sodium chloride (6M, 100 ml) and dried over magnesium sulphate. The solvent was removed by distillation and the residue purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (100:1) to give the novel compound 2'-acetyl-5'-methyl-N-methylformanilide, m.p. 58°-60°.

Workup

  1. temperaturecooled to 0 to 5° in an ice/salt bath
  2. stirringthe solution stirred at 20° for 3 hours
  3. temperatureThe reaction mixture was cooled to 0°
  4. temperaturewhilst maintaining the temperature below 8°
  5. temperaturewhilst maintaining the temperature below 10°
  6. extractionThe mixture was extracted with dichloromethane (3×30 ml)
  7. washThe combined extracts were washed with aqueous sodium chloride (6M, 100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customThe solvent was removed by distillation
  10. customthe residue purified by flash chromatography on a silica gel column
  11. washeluted with dichloromethane:methanol (100:1)

Sources & evidence

ORD record
ord-0217b2825e3448c3912021336c6d909f
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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