Hydrochloric Acid → 7-Chloroisoquinoline-3-carboxylic acid

HRID 1432890Notes

Reaction equation

HRID 1432890 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([CH:14]=[O:15])[N:10]=[CH:11]2)=[CH:6][CH:5]=1.CC[OH:18].Cl>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([C:14]([OH:18])=[O:15])[N:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 541450337-Chloroisoquinoline-3-carbaldehyde

Product 1

HCID 178423957-Chloroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 4.5 mL of a 1N NaOH solution at 0° C. is added a solution of AgNO3 (0.31 g, 1.8 mmol) in 3 mL of H2O, followed by a solution of of 7-chloro-isoquinoline-3-carbaldehyde (0.25 g, 1.3 mmol) in 3 of EtOH. The solution is stirred at 0° C. for 10 minutes, then at room temp. For 3 hours. The solution is acidified to pH=3 with 1H HCl. The resulting solution is extracted with CHCl3. The organic layer is dried over MgSO4, filtered and concentrated to give the product as a white solid (0.2 g, 0.96 mmol). 1H NMR (CD3OD, 300 MHz) δ9.18 (s, 1H), 8.63 (s, 1H), 8.18 (m, 1H), 7.80 (m, 2H), 6.94 (m, 1H), 4.15 (q, 2H), 3.48 (s, 2H), 1.20 (t, 3H). MS (EI): m/z 208, 210 (M+), Cl pattern.

Workup

  1. customat room temp
  2. waitFor 3 hours
  3. extractionThe resulting solution is extracted with CHCl3
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f0d52cd7acc4970b4e141bb8ee82b50
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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