Sodium Hydroxide → 4-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

HRID 1748245Notes

Reaction equation

HRID 1748245 reaction equation
[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:20])[NH:4][CH2:3]1.[OH-].[Na+]>C1COCC1.C(O)C>[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:20])[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67235749Ethyl 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

Product 1

HCID 587675714-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of ethyl 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate (3.2 g, 11.8 mmol) in THF:ethanol (1:1, 50 mL) is added 1N NaOH solution (43 mL, 43 mmol). The reaction mixture is heated at 75° C. for 18 h. The solvents are removed and the residue is dissolved in water. The aqueous solution is washed with ether and acidified to pH 4 using 3N HCl solution. The resulting white solid is filtered and rinsed more ether to afford the title compound (2.2 g, 76%).

Workup

  1. customThe solvents are removed
  2. dissolutionthe residue is dissolved in water
  3. washThe aqueous solution is washed with ether
  4. filtrationThe resulting white solid is filtered
  5. washrinsed more ether

Sources & evidence

ORD record
ord-a373eb7ff0054dc2a3579781626ad1c3
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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