Hydrochloric Acid → Pyrazino[1,2-a]indole-3-carboxylic acid hydrochloride

HRID 25160Notes

Reaction equation

HRID 25160 reaction equation
[CH:1]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH:4]=[C:3]([C:14]([O:16]CC)=[O:15])[N:2]=1.[OH-].[K+].O.[ClH:22]>CCO>[ClH:22].[CH:1]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH:4]=[C:3]([C:14]([OH:16])=[O:15])[N:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 12132803Ethyl pyrazino[1,2-a]indole-3-carboxylate

Product 1

HCID 69607038Pyrazino[1,2-a]indole-3-carboxylic acid hydrochlorideYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl pyrazino[1,2-a]indole-3-carboxylate (0.49 g, 2.0 mmol) in EtOH (30 mL) is added crushed potassium hydroxide (1.1 g, 20.0 mmol) followed by water (30 mL). The resulting dark colored solution is stirred at rt for 40 min and then neutralized with conc. HCl to pH ˜2. The acidic mixture is concentrated to dryness to afford pyrazino[1,2-a]indole-3-carboxylic acid hydrochloride. HRMS (FAB) calcd for C12H8N2O2+H 213.0664, found 213.0658.

Workup

  1. concentrationThe acidic mixture is concentrated to dryness

Sources & evidence

ORD record
ord-5b84bc6f76324c7bb22e155f3162326e
Source dataset
uspto-grants-2005_02
Patent number
US06858613B2

Reaction notes

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