Hydrochloric Acid → 3-Isoquinolinecarboxylic acid,1,2,3,4-tetrahydro-6-hydroxy-,hydrochloride

HRID 1199669Notes

Reaction equation

HRID 1199669 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].[CH2:14]=O.[ClH:16]>>[ClH:16].[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[CH2:14][NH:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6950578L-m-tyrosine

Product 1

HCID 129261753-Isoquinolinecarboxylic acid,1,2,3,4-tetrahydro-6-hydroxy-,hydrochloride

Procedure

To a mixture of 100.0 g of 3-hydroxyphenylalanine in 820 ml of 5% hydrochloric acid were added 78 ml of formaldehyde (37% in water). The reaction mixture was heated at 90°-95° C. (external bath temperature) for 45 minutes. The mixture was cooled and concentrated in vacuo. Five hundred milliliters of ethanol were added and the mixture was again concentrated in vacuo, affording 115 g of the title intermediate as a pale white solid, used without purification in the next step.

Workup

  1. temperatureThe reaction mixture was heated at 90°-95° C. (external bath temperature) for 45 minutes
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. additionFive hundred milliliters of ethanol were added
  5. concentrationthe mixture was again concentrated in vacuo

Sources & evidence

ORD record
ord-3e46a5c4658f44709ace3d572789c3f3
Source dataset
uspto-grants-1990_02
Patent number
US04902695

Reaction notes

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