Sodium Hydroxide → N-((6-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 2078039Notes

Reaction equation

HRID 2078039 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21]C)=[O:20])=[O:16])=[C:5]2[OH:23].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])=[C:5]2[OH:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67099712Methyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate

Product 1

HCID 54746528N-((6-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (0.256 g, 0.760 mmol) was suspended in water (3.0 mL) and treated with a 5N NaOH solution (0.38 mL, 1.90 mmol). After 20 minutes at ambient temperature, the resulting homogeneous mixture was quenched with a 1N HCl solution to pH=2. The white solid that precipitated upon acidification was collected by vacuum filtration and washed with 1:1 H2O/acetone (2×2.0 mL). The product was subsequently dried at 80° C. under vacuum for 24 hours. MS m/e=324.0 (M+H)+. Calculated for C15H14ClNO5 323.06.

Workup

  1. customthe resulting homogeneous mixture was quenched with a 1N HCl solution to pH=2
  2. customThe white solid that precipitated upon acidification
  3. filtrationwas collected by vacuum filtration
  4. washwashed with 1:1 H2O/acetone (2×2.0 mL)
  5. customThe product was subsequently dried at 80° C. under vacuum for 24 hours

Sources & evidence

ORD record
ord-00cb9d4ef59b4beabb236c9458e8dd1c
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…