Glyoxylic Acid → HCID 69199522, compound

HRID 896047Notes

Reaction equation

HRID 896047 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12](C(=O)C)[CH:11]=[CH:10]2>Cl>[ClH:6].[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N:12][CH:11]=[C:10]2[CH2:2][C:1]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 12624921HCID 12624921, compound

Product 1

HCID 69199522HCID 69199522, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Glyoxylic acid (1.37 g, 9.28 mmol) is added to mixture of 1-(6-chloro-1H-isoquinolin-2-yl)-ethanone [J. Org. Chem, 1980, 45, 1950] (1.44 g, 5.90 mmol) in 6N HCl (24 ml). The reaction is heated at 100° C. for 3 hours, cooled to RT, washed with ether and evaporated to 10 ml volume. After overnight refrigeration, the solid is collected by filtration and dried to afford (6-chloro-isoquinolin-4-yl)-acetic acid hydrochloride. 1H NMR (400 MHz, DMSO) δ: 4.45 (s 2H), 8.18 (d J 9 1H), 8.52 (s 1H), 8.70 (d J 8 1H), 8.83 (s 1H), 9.96 (s 1H).

Workup

  1. temperaturecooled to RT
  2. washwashed with ether
  3. customevaporated to 10 ml volume
  4. filtrationthe solid is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-6a5aba29ba5b487b89de9bd86df37d36
Source dataset
uspto-grants-2005_07
Patent number
US06919337B2

Reaction notes

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