Lithium Hydroxide → HCID 22184909, compound

HRID 348069Notes

Reaction equation

HRID 348069 reaction equation
C([O:3][C:4]([CH2:6][C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:8])=[O:5])C.[Li+].[OH-].OS([O-])(=O)=O.[Na+]>CO.O>[C:4]([CH2:6][C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:8])([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 17232026Ethyl 3-[(naphthalen-2-yl)amino]-3-oxopropanoate

Product 1

HCID 22184909HCID 22184909, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-((ethoxycarbonyl)methylcarbonylamino)naphthalene (2.3 g, 8.9 mmol) in MeOH (40 mL) was added a solution of LiOH (1.18 g, 27 mmol) in water (40 mL). The reaction mixture was stirred at ambient temperature. After 3 hours, the reaction mixture was acidified to pH 2–3 by 2N NaHSO4, then extracted with ethyl acetate (3×50 mL). The organic layer was dried over Na2SO4 and evaporated in vacuo to afford 2-((carboxy)methylcarbonyl-amino)naphthalene (2.0 g, 8.7 mmol) as a solid that was used in further preparations without further purification.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e8be5d34b26465ab86d6ec12b83f98d
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

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