Hydrochloric Acid → Lithium (4-oxo-4,5-dihydropyrrolo[2,3,4-ij] isoquinolin-1(3H)-yl)acetate

HRID 551044Notes

Reaction equation

HRID 551044 reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2[C:5]3=[C:6]([N:12]([CH2:14][C:15]([O:17]CC)=[O:16])[CH:13]=[C:4]3[NH:3]1)[CH:7]=[CH:8][CH:9]=2.[OH-].[Li+:21].Cl>C1COCC1.CCO.O>[O:1]=[C:2]1[CH2:11][C:10]2[C:5]3=[C:6]([N:12]([CH2:14][C:15]([O-:17])=[O:16])[CH:13]=[C:4]3[NH:3]1)[CH:7]=[CH:8][CH:9]=2.[Li+:21]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59257910Ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-if]isoquinolin-1(3H)-yl)acetate

Product 1

HCID 66636296Lithium (4-oxo-4,5-dihydropyrrolo[2,3,4-ij] isoquinolin-1(3H)-yl)acetate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-ij]isoquinolin-1(3H)-yl)acetate from Step G (200 mg, 0.77 mmol) in THF (1 mL), EtOH (1 mL) and H2O (1 mL) was added 1.0 N lithium hydroxide (0.85 mL, 0.85 mmol). After 15 min, 1 N aqueous HCl was added to adjust the solution to pH 7 and the mixture was concentrated in vacuo to give the title compound. MS: m/z=231 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d953f5319230411eb5303f1e9158075c
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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