Ammonia → HCID 178429547, compound

HRID 894842Notes

Reaction equation

HRID 894842 reaction equation
CO[C:3](=[O:7])[CH2:4][C:5]#[N:6].[NH3:8].C[O:10][C:11](=O)[CH2:12][C:13]([CH3:15])=O>O.S(=O)(=O)(O)O>[C:5]([C:4]1[C:3](=[O:7])[NH:8][C:11]([OH:10])=[CH:12][C:13]=1[CH3:15])#[N:6]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 7747Methyl cyanoacetateHCID 7757Methyl acetoacetate

Product 1

HCID 178429547HCID 178429547, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

3-cyano-4-methyl-6-hydroxypyrid-2-one is prepared by running 99 parts of cyanoacetic acid methyl ester into 160 parts of 24% strength aqueous ammonia, while stirring, at 10° to 15° C. The mixture is stirred for approx. 1 hour at 20° C., 133.5 parts of acetoacetic acid methyl ester are then added and the reaction mixture is heated at 80° C. for 4 hours in an autoclave, a maximum pressure of 1.5 bars being generated. The reaction suspension is then diluted with 400 parts of water and 114 parts of 61% strength sulphuric acid are added at 50°-60° C. and the mixture is cooled to 20° C. The product precipitated is filtered off, washed with water and dried. This gives 147.0 parts (98% of theory) of 3-cyano-4-methyl-6-hydroxypyrid-2-one with a melting point above 305° C.

Workup

  1. custom3-cyano-4-methyl-6-hydroxypyrid-2-one is prepared
  2. stirringThe mixture is stirred for approx. 1 hour at 20° C.
  3. additionare added at 50°-60° C.
  4. temperaturethe mixture is cooled to 20° C
  5. customThe product precipitated
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e17317357fed4ef8959f357b3af6ca26
Source dataset
uspto-grants-1981_08
Patent number
US04284782

Reaction notes

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