Hydrochloric Acid → HCID 66743147, compound

HRID 2363926Notes

Reaction equation

HRID 2363926 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([O:16]C)=[O:15].C[O-].[Na+].CO.Cl>O>[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[S:5][C:4]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 66743684HCID 66743684, compound

Product 1

HCID 66743147HCID 66743147, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate (0.533 g, 2.15 mmol), sodium methoxide (0.348 g, 6.45 mmol), methanol (8.0 mL) and water (2.0 mL) was heated at reflux for 4 h. The mixture was cooled in an ice-bath and conc. HCl (0.533 mL, 6.45 mmol) was added to adjust the pH to 4. The resultant yellow precipitate was collected by filtration and washed with water and methanol to afford the title compound (0.342 g, 68%) as a yellow solid:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureThe mixture was cooled in an ice-bath
  4. filtrationThe resultant yellow precipitate was collected by filtration
  5. washwashed with water and methanol

Sources & evidence

ORD record
ord-25f85a26cf024881b1a3cfbd5c4325ce
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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