Water → HCID 21251118, compound

HRID 1737653Notes

Reaction equation

HRID 1737653 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[C:14]([C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([O:26][CH3:27])[C:19]=1[NH:28]C(=O)OC(C)(C)C)([O:16][CH3:17])=[O:15].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[NH2:28][C:19]1[C:20]([O:26][CH3:27])=[N:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21251110HCID 21251110, compound

Product 1

HCID 21251118HCID 21251118, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

p-Toluene sulfonic acid hydrate (0.282 g, 1.48 mmol) was dissolved in toluene (11 mL) and heated to reflux overnight with azeotropic removal of H2O (Dean-Stark trap). The next day, the reaction was cooled to room temperature and the product of Example 28, dissolved in toluene (4 mL), was added. The reaction was heated back to reflux for 0.5 hours. The reaction was cooled to room temperature and poured into NaHCO3 (sat) and extracted 3 times with ether. The organics were combined, washed with brine, dried over MgSO4, concentrated in vacuo. The residue was purified by column chromatography using hexane/ethyl acetate as eluant (gradient 100% to 9/1) to provide 0.278 g (97%) of methyl 3-amino-2,6-dimethoxyisonicotinate as a yellow solid. Electrospray Mass Spec: 212.8 (M+H)+

Workup

  1. temperatureheated
  2. additionwas added
  3. temperatureThe reaction was heated back
  4. temperatureto reflux for 0.5 hours
  5. temperatureThe reaction was cooled to room temperature
  6. extractionextracted 3 times with ether
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4c58f907648c47d3b9b564ce3ec920f5
Source dataset
uspto-grants-1999_10
Patent number
US05962481

Reaction notes

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