Perchloric Acid → 1-amino-4-(methoxycarbonyl)pyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate

HRID 874416

Reaction equation

HRID 874416 reaction equation
Cl(O)(=O)(=O)=O.[C:6]1([CH3:24])[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[S:14]([O:17]/[N:18]=C(\OCC)/C)(=[O:16])=[O:15].[NH2:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][N:35]=1)[C:29]([O:31][CH3:32])=[O:30].NC1C=C(C=CN=1)C([O-])=O>C(Cl)Cl.C(OC)(C)(C)C.O.O1CCOCC1>[CH3:13][C:8]1[CH:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH3:24])[C:7]=1[S:14]([O-:17])(=[O:16])=[O:15].[NH2:18][N:35]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]1=[NH2+:25]

Participants

9

Reactant 4

HCID 24247Perchloric AcidHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 5748625ethyl (1E)-N-{[(2,4,6-trimethylphenyl)sulfonyl]oxy}ethanimidateHCID 231716212-Aminoisonicotinate

Product 1

HCID 1784984591-amino-4-(methoxycarbonyl)pyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonateYield 88.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
3 °C

Procedure

70% Perchloric acid (18.9 ml) was added to a 1,4-dioxane (26 ml) solution of (Z)-ethyl N-(mesitylsulfonyl)oxyacetimidate (11.7 g) at 4° C. over 20 minutes. Thereafter, the reaction solution was stirred at 3° C. for 30 minutes, and it was then poured into water (100 ml). The precipitated solid was collected by filtration, and was then washed with water (45 ml) to obtain a white solid as a crude product. Methyl 2-aminoisonicotinate (5 g) was added to methylene chloride (35 ml), and the obtained mixture was then cooled to 3° C. The obtained crude product was dissolved in methylene chloride (40 ml), and only an organic layer was added to a methylene chloride solution of 2-aminoisonicotinate. The obtained mixture was stirred at 3° C. for 30 minutes. Thereafter, methyl tert-butyl ether (50 ml) was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was washed with methyl tert-butyl ether (20 ml), and was then dried at 45° C., so as to obtain the title compound (10.7 g) in the form of a light yellow solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwas then washed with water (45 ml)
  3. customto obtain a white solid as a crude product
  4. temperaturethe obtained mixture was then cooled to 3° C
  5. customThe obtained crude product
  6. stirringThe obtained mixture was stirred at 3° C. for 30 minutes
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe collected solid was washed with methyl tert-butyl ether (20 ml)
  9. customwas then dried at 45° C.

Sources & evidence

ORD record
ord-f8413180f87045898dcabba00f86e1b7
Source dataset
uspto-grants-2015_03
Patent number
US08980889B2

Linked notes

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