Sodium Hydroxide → 2-Amino-5-(4-fluorophenyl)thiophene-3-carboxylic acid

HRID 1658370Notes

Reaction equation

HRID 1658370 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21529229Ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate

Product 1

HCID 215292312-Amino-5-(4-fluorophenyl)thiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-amino-5-(4-fluorophenyl)- 3-thiophene carboxylate (2g), sodium hydroxide (1g) and ethanol (20 ml) was refluxed for 5 hours, cooled and then concentrated. The solid residue was dissolved in water, filtered and acidified at 0°C. The light brown precipitate was collected by filtration to give pure 2-amino-5-(4-fluorophenyl)- 3-thiophene carboxylic acid, m.p. 172°-4°.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe solid residue was dissolved in water
  5. filtrationfiltered
  6. customacidified at 0°C
  7. filtrationThe light brown precipitate was collected by filtration

Sources & evidence

ORD record
ord-6ba0a936184b4e70902040b64275cb12
Source dataset
uspto-grants-1976_06
Patent number
US03963750

Reaction notes

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