Hydrochloric Acid → 3-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid

HRID 2363943Notes

Reaction equation

HRID 2363943 reaction equation
[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([O:17]C)=[O:16])[CH3:2].C[O-].[Na+].CO.Cl>O>[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([OH:17])=[O:16])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 66743314Methyl 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate

Product 1

HCID 667437393-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acidYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate (0.636 g, 2.42 mmol), sodium methoxide (0.393 g, 7.27 mmol), methanol (10 mL) and water (2.5 mL) was refluxed overnight. The mixture was cooled in an ice-bath and conc. HCl (0.600 mL, 7.27 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 (0.415 g, 69%) as an orange solid:

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe mixture was cooled in an ice-bath
  3. filtrationThe resultant yellow precipitate was collected by filtration
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-c294efc1d75649a0a191f83c2a8d13f0
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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