Hydrochloric Acid → HCID 5061798, compound

HRID 2206516Notes

Reaction equation

HRID 2206516 reaction equation
[CH3:1]O.[CH3:3][C:4]1[N:5]([CH2:17][C:18]2C=NC=NC=2)[C:6]2[C:11]([C:12]=1[C:13]([O:15]C)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[OH-].[K+].Cl>O>[CH:17]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([C:13]([OH:15])=[O:14])=[C:4]1[CH3:3])([CH3:18])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 117779002HCID 117779002, compound

Product 1

HCID 5061798HCID 5061798, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of methanol (10 mL) and water (2 mL), methyl 2-methyl-1-(pyrimidin-5-ylmethyl)-1H-indole-3-carboxylate (110 mg, 0.39 mmol) and potassium hydroxide (50 mg, 0.98 mmol) was added. The mixture was stirred at reflux for 12 hours. Then the reaction mixture was acidified by hydrochloric acid aqueous solution (1N) to adjust pH=6 and extracted with dichloromethane (10 mL*3). The organic layers were combined and concentrated to give 1-isopropyl-2-methyl-1H-indole-3-carboxylic acid (60 mg, 58%).

Workup

  1. temperatureat reflux for 12 hours
  2. extractionextracted with dichloromethane (10 mL*3)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2bf233c5b95249d9b1c3d80f6b7f7bcf
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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