2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one → 5-(2-Oxopropoxy)salicylamide

HRID 4553Notes

Reaction equation

HRID 4553 reaction equation
CC1(C)[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([O:13][CH2:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][C:4]=2[O:3]1>O1CCOCC1.Cl>[O:17]=[C:15]([CH3:16])[CH2:14][O:13][C:10]1[CH:9]=[C:5]([C:6]([NH2:7])=[O:8])[C:4]([OH:3])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 137543322,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one

Product 1

HCID 137543335-(2-Oxopropoxy)salicylamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

74 g of the resulting 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one in a mixture of 150 ml of dioxane and 450 ml of 2N hydrochloric acid are heated for 45 minutes on a water bath. The solvent is evaporated off, and the crystalline residue is triturated with water and then filtered off with suction. Recrystallisation from isopropanol yields 5-(2-oxo-propoxy)-salicylamide, which has a melting point of 152°-154°.

Workup

  1. temperatureare heated for 45 minutes on a water bath
  2. customThe solvent is evaporated off
  3. customthe crystalline residue is triturated with water
  4. filtrationfiltered off with suction
  5. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-364286022957480fb90d4b28428360df
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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