Hydrochloric Acid → Aminocyclopyrachlor-methyl

HRID 907430Notes

Reaction equation

HRID 907430 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[N:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[N:8]=[C:7]([C:14]([O:16][CH2:17]C)=[O:15])[C:6]=1[Cl:19].Cl.[Cl-].[NH4+]>CO>[NH2:4][C:5]1[N:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[N:8]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[C:6]=1[Cl:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 11989828Ethyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate2×

Product 1

HCID 16725794Aminocyclopyrachlor-methylYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 887MethanolSolvent2×

Procedure

Sodium methoxide in methanol (25%, 3 drops) was added to ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate (i.e. the product of Example 7) (0.53 g) in methanol (15 mL). The mixture was boiled for 1 h. The mixture was allowed to cool to room temperature, and was partitioned between hydrochloric acid (0.28 g, 1.16 mmol) in methanol (5 mL). The mixture was boiled for 90 minutes. The mixture was allowed to cool to room temperature, and ammonium chloride (0.3 g, 5.6 mmol) was added. After 10 minutes the solvent was removed under reduced pressure. The mixture was extracted with ethyl acetate (50 mL), and the extracts evaporated to give the product as a white solid (0.24 g, 92% yield). Product recrystallized from ethyl acetate melted at 148.5-149.5° C.

Workup

  1. waitThe mixture was boiled for 90 minutes
  2. temperatureto cool to room temperature
  3. customAfter 10 minutes the solvent was removed under reduced pressure
  4. extractionThe mixture was extracted with ethyl acetate (50 mL)
  5. customthe extracts evaporated

Sources & evidence

ORD record
ord-19bc1b4b31d0447b8a2d38718f7f72b6
Source dataset
uspto-grants-2011_09
Patent number
US08013155B2

Reaction notes

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