Hydrochloric Acid → HCID 70029245, compound

HRID 334055Notes

Reaction equation

HRID 334055 reaction equation
N(OC(C)(C)C)=O.[CH3:8][O:9][C:10]([C:12]1[CH:17]=[C:16](N)[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1)=[O:11].[ClH:21]>C(#N)C.[Cu](Cl)Cl>[CH3:8][O:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:21])[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1)=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 84070846HCID 84070846, compound

Product 1

HCID 70029245HCID 70029245, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 1.25 mL (10.5 mmol) tert-butyl nitrite and 1.42 g (10.5 mmol) copper(II)chloride in 40 mL acetonitrile was added a solution of 1.20 g (6.59 mmol) 4-amino-6-methoxy-pyridine-2-carboxylic acid methyl ester in 10 mL acetonitrile dropwise at 40° C. This mixture was stirred at 80° C. for 1 h, then poured into ice water, acidified with 4 M aqueous HCl and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=3/1→2/1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (PE/EtOAc=3/1→2/1)

Sources & evidence

ORD record
ord-1ad606638b5941468860b7f4f3c80270
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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