Hydrochloric Acid → 3-Amino-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

HRID 487724Notes

Reaction equation

HRID 487724 reaction equation
[OH-].[Na+].C([N:6]1[CH2:11][CH2:10][C:9]2[S:12][C:13]([C:16]([O:18]C)=[O:17])=[C:14]([NH2:15])[C:8]=2[CH2:7]1)(=O)C.Cl>O>[NH2:15][C:14]1[C:8]2[CH2:7][NH:6][CH2:11][CH2:10][C:9]=2[S:12][C:13]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19093041HCID 19093041, compound

Product 1

HCID 190930483-Amino-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous solution obtained by dissolving 9.1 g of sodium hydroxide in 90 ml of water was added to 5.8 g (46%) of methyl 5-acetyl-3-amino-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2carboxylate (Compound No. 16) obtained in Example 1 and the resultant mixture was heated under reflux for 2 hours. After cooling followed by neutralization with concentrated hydro-chloric acid, the solvent was distilled off. Methanol was added to the residue and the crystals thus formed were taken by filtration and thoroughly washed with water to obtain 1.7 g of 3-amino-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid. Yield: 38%.

Workup

  1. customAn aqueous solution obtained
  2. custom16) obtained in Example 1
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling
  5. distillationthe solvent was distilled off
  6. additionMethanol was added to the residue
  7. customthe crystals thus formed
  8. filtrationwere taken by filtration
  9. washthoroughly washed with water

Sources & evidence

ORD record
ord-a3579ee4f44d431d939910645b17cdb5
Source dataset
uspto-grants-1994_03
Patent number
US05296603

Reaction notes

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