Acetic Anhydride → HCID 23471553, compound

HRID 128021Notes

Reaction equation

HRID 128021 reaction equation
[OH:1][CH2:2][CH:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)=[N:7][NH:6][C:5](=[O:21])[CH2:4]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:22]([O:1][CH2:2][CH:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)=[N:7][NH:6][C:5](=[O:21])[CH2:4]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23471568HCID 23471568, compound

Product 1

HCID 23471553HCID 23471553, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 13.6 g of 6-(5-hydroxymethyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1-methyl-1,2,3,4-tetrahydroquinolin-2-one, 5.8 g of acetic anhydride and 10 ml of triethylamine in 300 ml of chloroform was heated under reflux on a water bath for 3 hours. The reaction mixture was washed with water, dried over potassium carbonate and concentrated under reduced pressure. The residue was dissolved into a small amount of ethyl acetate. After the solution was allowed to stand, the precipitated crystals were filtered off and recrystallized from isopropanol to give 7.3 g of 6-(5-acetoxymethyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1-methyl-1,2,3,4-tetrahydroquinolin-2-one as needles, melting at 149°-153° C.

Workup

  1. temperatureunder reflux on a water bath for 3 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over potassium carbonate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved into a small amount of ethyl acetate
  6. filtrationthe precipitated crystals were filtered off
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-2460886106524f7ba1b851a1747efc93
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

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