Hydrochloric Acid → HCID 54097963, compound

HRID 2286675Notes

Reaction equation

HRID 2286675 reaction equation
C([O:3][C:4](=[O:18])[C:5]([C:9]1[N:14]=[C:13]([NH:15]C=O)[CH:12]=[CH:11][N:10]=1)=[N:6][O:7][CH3:8])C.[OH-].[K+].Cl>C(O)C>[NH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([C:5](=[N:6][O:7][CH3:8])[C:4]([OH:18])=[O:3])[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54343679HCID 54343679, compound

Product 1

HCID 54097963HCID 54097963, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-formamidopyrimidin-2-yl)-2-methoxyiminoacetic acid (syn isomer) (30.8 g) in ethanol (308 ml) was added 1 N alcoholic solution (550 ml) of potassium hydroxide and the mixture was stirred for 3.5 hours at ambient temperature. The reaction mixture was cooled in an ice bath and adjusted to pH3 with concentrated hydrochloric acid (53 ml). The resultant solid was filtered and washed with ethanol (60 ml), water (100 ml), acetone (100 ml) to give a crude product (28.8 g). This product (1 g) was recrystallized from water (10 ml) to give a purified product of 2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetic acid (dihydrate, syn isomer) (0.4 g), mp. 178°-183° C. (dec.).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationThe resultant solid was filtered
  3. washwashed with ethanol (60 ml), water (100 ml), acetone (100 ml)
  4. customto give a crude product (28.8 g)
  5. customThis product (1 g) was recrystallized from water (10 ml)

Sources & evidence

ORD record
ord-b3fab66ff29a43c1b3c7bfe3fd1b94c0
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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