Cyanoacetamide → 5-Acetyl-2-hydroxy-6-methylnicotinonitrile

HRID 1649152Notes

Reaction equation

HRID 1649152 reaction equation
COC(OC)N(C)C.CC(=O)CC(=O)C.CN([CH:19]=[C:20]([C:24](=O)[CH3:25])[C:21](=[O:23])[CH3:22])C.C[O-].[Na+].[C:30]([CH2:32][C:33]([NH2:35])=[O:34])#[N:31]>C(O)(=O)C.O.CO>[C:21]([C:20]1[CH:19]=[C:32]([C:30]#[N:31])[C:33](=[O:34])[NH:35][C:24]=1[CH3:25])(=[O:23])[CH3:22]

Participants

9

Reactant 5

HCID 7898CyanoacetamideHCID 31261AcetylacetoneHCID 78373Dimethylformamide dimethyl acetalHCID 5670033-[(Dimethylamino)methylidene]pentane-2,4-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution containing 60 g of dimethylformamide dimethyl acetal and 50 g of 2,4-pentanedione was heated on a steam bath for 2.5 hours and cooled. To the resulting solution containing 3-dimethylaminomethylene-2,4-pentanedione was added 300 ml of methanol, 27 g of sodium methoxide and 47 g of cyanoacetamide. The resulting mixture was heated on a steam bath for 4 hours, the hot solution poured into 700 ml of water, and the aqueous mixture acidified with acetic acid and chilled in an ice bath. The solid that separated was collected, dried, and heated with 400 ml. of methanol. Insoluble material was filtered from the hot methanol mixture and the filtrate cooled. The product that separated was collected and dried at 90° C. to produce 24.6 g of 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinonitrile, m.p. 227°-230° C. [Sunthankar et al., supra, m.p. 231° C.]

Workup

  1. temperaturewas heated on a steam bath for 2.5 hours
  2. temperaturecooled
  3. temperatureThe resulting mixture was heated on a steam bath for 4 hours
  4. temperaturechilled in an ice bath
  5. customThe solid that separated
  6. customwas collected
  7. customdried
  8. temperatureheated with 400 ml
  9. filtrationInsoluble material was filtered from the hot methanol mixture
  10. temperaturethe filtrate cooled
  11. customThe product that separated
  12. customwas collected
  13. customdried at 90° C.

Sources & evidence

ORD record
ord-ecdce4c6bb24458ab4b4d0f3db67ab08
Source dataset
uspto-grants-1983_11
Patent number
US04415580

Reaction notes

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