Hydrochloric Acid → 1,2,3,4-Tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid, methyl ester, hydrochloride

HRID 868164Notes

Reaction equation

HRID 868164 reaction equation
[ClH:1].[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[CH2:9][NH:8][CH:7]([C:14]([OH:16])=[O:15])[CH2:6]2.[CH3:17]O>>[ClH:1].[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[CH2:9][NH:8][CH:7]([C:14]([O:16][CH3:17])=[O:15])[CH2:6]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 129261581,2,3,4-Tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid

Product 1

HCID 667196951,2,3,4-Tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid, methyl ester, hydrochloride

Procedure

At 40° C., a steam of gaseous hydrogen chloride was bubbled through a solution of 1,2,3,4-tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid (32.4 g, 155.0 mmol) in 1.5 l of methanol for 2 hours. After stirring overnight at room temperature, the solvent was distilled off in vacuo and the residue triturated with ether to furnish 38.95 g of the product. Melting point 204.8° C.

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-3342dbfd685746c9a341683f6b981c56
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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