Methanol → 3-{[2-(Methyloxy)ethyl]amino}-1-naphthalenecarboxylic acid

HRID 337596Notes

Reaction equation

HRID 337596 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:16]([O:18]C)=[O:17])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.CO.[Li+].[OH-]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:16]([OH:18])=[O:17])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66896921Methyl 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylate

Product 1

HCID 668958083-{[2-(Methyloxy)ethyl]amino}-1-naphthalenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylate (1 eq.) from the previous step was taken up in a 2:1 (v/v) mixture of MeOH:THF (0.08 M). To this solution was then added LiOH (1.0 M aq. solution, 3.4 eq.) and the resulting cloudy solution was vigorously stirred at RT for 16 h. The volatiles were then removed in vacuo and the pH of the residue was carefully adjusted to ˜2 with 1 N aq. HCl before it was extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a yellow solid.

Workup

  1. customThe volatiles were then removed in vacuo
  2. extractionwas extracted with EtOAc
  3. washThe combined organic extracts were washed further with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-705ac83ed4364129872b8b3e896d8bd7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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