Ethyl Acetoacetate → HCID 19967112, compound

HRID 326269Notes

Reaction equation

HRID 326269 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O=[C:15]([CH3:22])[CH2:16][C:17](OCC)=[O:18].C(=O)([O-])[O-].[K+].[K+]>O>[N:1]1([CH2:6][C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[NH:13][C:15]([CH3:22])=[CH:16][C:17]3=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11430Potassium CarbonateHCID 12653194-Imidazol-1-ylmethylphenylamine

Product 1

HCID 19967112HCID 19967112, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and heated (100° C.) solution of 10 parts of 4-(1H-imidazol-1-ylmethyl)-benzenamine in 50 parts of poly phosphoric acid were added 15 parts of ethyl 3-oxobutanoate. The whole was stirred for 4 hours at 140° C. 100 Parts of water were added to the mixture and the whole was neutralized with potassium carbonate. The product was extracted with a mixture of ethyl acetate and methanol. The extract was dried, filtered and concentrated. The concentrate was crystallized from a mixture of 2-propanone and methanol. The product was filtered off and dried, yielding 2 parts (14.4%) of 6-(1H-imidazol-1-ylmethyl)-2-methyl-4(1H)quinolinone; mp. 245.5° C. (decomp.) (compound 77).

Workup

  1. stirringThe whole was stirred for 4 hours at 140° C
  2. extractionThe product was extracted with a mixture of ethyl acetate and methanol
  3. customThe extract was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was crystallized from a mixture of 2-propanone and methanol
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-0aeab11310a54abebddf09f24399ae11
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Reaction notes

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