Lithium Hydroxide → N-Naphthalen-1-yl-oxalamic acid
Reaction equation
C[O:2][C:3](=[O:17])[C:4]([NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:5].[OH-].[Li+]>C1COCC1>[C:7]1([NH:6][C:4](=[O:5])[C:3]([OH:17])=[O:2])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To N-Naphthalen-1-yl-oxalamic acid methyl ester (0.14 g, 0.61 mmol) stirring in THF (2 mL) was added 2 mL of a 1N lithium hydroxide solution. The reaction was heated to 50° C. and stirred for 2 h. The resulting mixture was concentrated in vacuo to afford a yellow residue that was acidified with 1N HCL. The resulting mixture was extracted with DCM (3×50 mL), dried over MgSO4 and concentrated under vacuum to afford crude product. The crude material was purified by flash chromatography (0-20% MeOH:DCM, silica gel) to afford the desired product (0.128 g, 98%) as a thick oil. Expected mass=215. Observed mass=216.
Workup
- concentrationThe resulting mixture was concentrated in vacuo
- customto afford a yellow residue that
- extractionThe resulting mixture was extracted with DCM (3×50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuum
- customto afford crude product
- customThe crude material was purified by flash chromatography (0-20% MeOH:DCM, silica gel)
Sources & evidence
- ORD record
- ord-0cedf2ea6fa046d3916e4b14ce89bd4f
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07749999B2
Reaction notes
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