Sulfuric Acid → HCID 19967123, compound

HRID 326268Notes

Reaction equation

HRID 326268 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[CH2:15][C:16](=O)[CH3:17])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[OH-].[NH4+]>>[N:1]1([CH2:6][C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[NH:13][C:14](=[O:19])[CH:15]=[C:16]3[CH3:17])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 19967135HCID 19967135, compound

Product 1

HCID 19967123HCID 19967123, compoundYield 34.8%

Conditions

Temperature
70 °C

Procedure

7 Parts of N-[4-(1H-imidazol-1-ylmethyl)phenyl]-3-oxobutanamide were added dropwise to 73.6 parts of concentrated sulfuric acid (exothermic reaction, the temperature rose to 90° C.). Upon complete addition, the mixture was stirred for 1 hour at 70° C. The reaction mixture was poured into crushed ice and the whole was neutralized with an ammonium hydroxide solution to pH 9. The precipitated product was filtered off and taken up in water. The whole was extracted with dichloromethane. The aqueous layer was concentrated. The crystallized product was filtered off, washed with 2-propanone and dried in vacuo at 100° C., yielding 2.25 parts (34.8%) of 6-(1H-imidazol-1-ylmethyl)-4-methyl-2(1H)-quinolinone; mp. 266.0° C. (compound 1).

Workup

  1. customexothermic reaction
  2. customrose to 90° C.
  3. additionUpon complete addition
  4. additionThe reaction mixture was poured
  5. custominto crushed ice
  6. filtrationThe precipitated product was filtered off
  7. extractionThe whole was extracted with dichloromethane
  8. concentrationThe aqueous layer was concentrated
  9. filtrationThe crystallized product was filtered off
  10. washwashed with 2-propanone
  11. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-56ca99aa703b45168f02906c5792c140
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Reaction notes

Loading…