Pyridine → HCID 19816038, compound

HRID 2247908Notes

Reaction equation

HRID 2247908 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH:16]([O:19][CH3:20])[O:17][CH3:18].N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28]>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:27](=[O:29])[CH3:28])=[C:3]([CH:16]([O:17][CH3:18])[O:19][CH3:20])[CH:4]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 19816065HCID 19816065, compound

Product 1

HCID 19816038HCID 19816038, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (10° C.) solution of 22.1 parts of intermediate 64, namely [4-amino-3-(dimethoxymethyl)phenyl] phenylmethanone, in 147 parts of pyridine were added dropwise 12.1 parts of acetyl chloride. After stirring for 1/2 hour at 10° C. and overnight at room temperature, the reaction mixture was poured into water. The product was extracted with 2,2'-oxybispropane and dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was dissolved in dichloromethane. This solution was washed successively with HCl 0.1N, ammonia and water and was then dried, filtered and evaporated, yielding 27.5 parts (100%) of N-[4-benzoyl-2-(dimethoxymethyl)phenyl]acetamide (interm. 65).

Workup

  1. stirringAfter stirring for 1/2 hour at 10° C. and overnight at room temperature
  2. extractionThe product was extracted with 2,2'-oxybispropane and dichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washThis solution was washed successively with HCl 0.1N, ammonia and water
  8. customwas then dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-1a7c8811833746268a924c4c59c49c68
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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