Lithium hydroxide, monohydrate → 5-(2-Ethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH:17][CH2:18][CH3:19])=O)C.O.[OH-].[Li+]>C(O)(=O)C(O)=O>[CH2:18]([NH:17][CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][C:7]2[NH:8][CH:9]=[C:10]([CH3:11])[C:6]=2[C:4]1=[O:3])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
A stirred mixture of 2-[2-(2-ethylamino-ethylamino)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (400 mg, 1.498 mmol), lithium hydroxide monohydrate (503 mg, 11.985 mmol) in 25 ml of oxalic acid was heated to reflux at 135° C. The mixture was concentrated under reduced pressure, added with water (10 ml) and extracted with dichloromethane (20 ml×3). The combined extracts Were dried over anhydrous magnesium sulfate, filtered and concentrated wider reduced pressure to give 5-(2-ethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one (100 mg, 30.2%) as a brown oil.
Workup
- temperaturewas heated
- concentrationThe mixture was concentrated under reduced pressure
- additionadded with water (10 ml)
- extractionextracted with dichloromethane (20 ml×3)
- dry with materialThe combined extracts Were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated wider reduced pressure
Sources & evidence
- ORD record
- ord-875196dd6c3a4e05aaf8b4074b4bbe06
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697692B2
Reaction notes
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