Hydrochloric Acid → Formamide, N-(2-acetylphenyl)-N-methyl-

HRID 358659Notes

Reaction equation

HRID 358659 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[CH3:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=O)[CH3:17].[OH-:19].[Na+].Cl>ClCCl.O.C(O)=O>[C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:9]([CH3:8])[CH:5]=[O:7])(=[O:19])[CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 155795831-[2-(Methylamino)phenyl]ethan-1-one

Product 1

HCID 12261279Formamide, N-(2-acetylphenyl)-N-methyl-

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of acetic anhydride (147.2 ml) and formic acid (98%, 100.3 ml) was stirred at 50°-60° for 110 minutes and then cooled to ambient temperature. 2'-(Methylamino)acetophenone (100 g) was added in portions over a period of 30 minutes whilst maintaining the temperature below 30°. The mixture was stirred at ambient temperature for 90 minutes and then cooled to 0°. Water (512 ml) was added over a period of 20 minutes, followed by aqueous sodium hydroxide (specific gravity 1.5, 288 ml) added over a period of 85 minutes whilst maintaining the temperature below 10°. The reaction mixture was transferred to a separating funnel, dichloromethane (200 ml) was added, followed by hydrochloric acid (2M) to pH 9, and the dichloromethane layer separated. The aqueous layer was further extracted with dichloromethane (2×200 ml). The combined dichloromethane extracts were washed with aqueous sodium chloride (6M, 200 ml) and then dried over magnesium sulphate to give a solution of 2'-acetyl-N-methylformanilide.

Workup

  1. temperaturewhilst maintaining the temperature below 30°
  2. stirringThe mixture was stirred at ambient temperature for 90 minutes
  3. temperaturecooled to 0°
  4. additionadded over a period of 85 minutes
  5. temperaturewhilst maintaining the temperature below 10°
  6. customThe reaction mixture was transferred to a separating funnel
  7. customthe dichloromethane layer separated
  8. extractionThe aqueous layer was further extracted with dichloromethane (2×200 ml)
  9. washThe combined dichloromethane extracts were washed with aqueous sodium chloride (6M, 200 ml)
  10. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-959d62569e7d48969de5b24caea29faf
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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