Hydrochloric Acid → 2-Naphthoylglycine

HRID 1351142Notes

Reaction equation

HRID 1351142 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][NH:5][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[O:7].[OH-].[Na+].Cl.CO>O>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:6]([NH:5][CH2:4][C:3]([OH:18])=[O:2])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19789839HCID 19789839, compound

Product 1

HCID 1296712-NaphthoylglycineYield 53.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

[(Naphthalene-2-carbonyl)amino]acetic acid methyl ester (10.03 g, 41 mmol, 1.0 eq., see step (a) above) was added to the flask followed by aqueous sodium hydroxide (1 M, 120 mL, 123 mmol, 3.0 eq.). The mixture was heated to 55° C. using an oil bath for 2 hours. The mixture was cooled to 5° C. using an ice/water bath. Concentrated hydrochloric acid (50 mL) was added very slowly to the cooled solution, ensuring that the temperature did not rise above 10° C. A dense yellow precipitate was formed. The mixture was stirred for 10 minutes and was then filtered. The yellow solid was air lo dried for 15 minutes and then dried in vacuo at 40° C. for 16 hours (8.73 g, 93%). Methanol (50 mL, 10 vols) and water (100 ml, 20 vols) were added to a portion of the sub-title compound (5.0 g, 22 mmol). The mixture was heated to 70° C. using an oil bath whilst being stirred. The solution was held at this temperature for 10 minutes, and then was allowed to cool further to 5° C. using an ice/water bath. Crystallisation began at approximately 30° C. The precipitate was collected by filtration, air dried for 15 minutes, then dried in vacuo at 40° C. for 2 hours (3.2 g, 64%). The isolated sub-title compound (3.2 g, 0.014 mol, 64%) was added to water (100 mL, 20 vols) and methanol (50 mL, 10 vols). The mixture was heated to 70° C. to dissolve the solid. The solution was allowed to cool to room temperature, crystallisation occurred on cooling. The mixture was cooled further to 2° C., and then was filtered using a sinter funnel. The solid was air dried for 10 minutes, then dried in vacuo at 40° C. for 16 hours (2.21 g, 44%).

Workup

  1. customfor 2 hours
  2. temperatureThe mixture was cooled to 5° C.
  3. customdid not rise above 10° C
  4. customA dense yellow precipitate was formed
  5. filtrationwas then filtered
  6. customdried for 15 minutes
  7. customdried in vacuo at 40° C. for 16 hours (8.73 g, 93%)

Sources & evidence

ORD record
ord-a55732cffce64b498dc0bc4c0e9b66a8
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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