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

HRID 2363952
Notes
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Reaction equation

HRID 2363952 reaction equation
[CH2:1]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([O:19]C)=[O:18])[CH2:2][CH2:3][CH3:4].C[O-].[Na+].CO.Cl>O>[CH2:1]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([OH:19])=[O:18])[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 66743415Methyl 3-(butylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate

Product 1

HCID 667438043-(Butylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of methyl 3-(butylamino)-5-(pyridin-4-yl)thiophene-2-carboxylate (0.460 g, 1.58 mmol), sodium methoxide (0.257 g, 4.75 mmol), methanol (6.4 mL) and water (1.6 mL) was refluxed overnight. The mixture was cooled in an ice-bath and conc. HCl (0.390 mL, 4.75 mmol) was added. The resultant yellow precipitate was collected by filtration and washed with water and methanol to afford the title compound (0.370 g, 85%) as a yellow 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-992f41a196e842cca866dfdd865bbef6
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691828B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes