HCID 22139808, compound → methyl 3-amino-4-chlorothiophene-2-carboxylate

HRID 1825915Notes

Reaction equation

HRID 1825915 reaction equation
C([NH:4][C:5]1[C:9]([Cl:10])=[CH:8][S:7][C:6]=1[C:11]([O:13][CH3:14])=[O:12])(=O)C>CO.Cl>[NH2:4][C:5]1[C:9]([Cl:10])=[CH:8][S:7][C:6]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 22139808HCID 22139808, compound

Product 1

HCID 22139844methyl 3-amino-4-chlorothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a mixture of 50 ml of methanol and 50 ml of concentrated hydrochloric acid, 7 g of methyl 3-acetylamino-4-chlorothiophene-2-carboxylate are stirred at 60° C. for 4 hours, under reflux for 5 hours and at room temperature for another 3 days. Any precipitate that has formed is removed by filtration, and about ⅓ of the volume of the solvent is removed by distillation under reduced pressure. Following addition of about 100 ml of water, the mixture is stirred at room temperature for another 15 minutes and the colorless crystals are filtered off and dried in a stream of air. M.p.: 62-64° C.

Workup

  1. temperatureunder reflux for 5 hours and at room temperature for another 3 days
  2. customAny precipitate that has formed
  3. customis removed by filtration
  4. customabout ⅓ of the volume of the solvent is removed by distillation under reduced pressure
  5. additionaddition of about 100 ml of water
  6. stirringthe mixture is stirred at room temperature for another 15 minutes
  7. filtrationthe colorless crystals are filtered off
  8. customdried in a stream of air

Sources & evidence

ORD record
ord-d9754836ba144af19fbd90f03888f088
Source dataset
uspto-grants-2006_05
Patent number
US07049333B2

Reaction notes

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