Lithium Hydroxide → 8-(Aminomethyl)naphthalene-2-carboxylic acid

HRID 1417909Notes

Reaction equation

HRID 1417909 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[CH:9]=[CH:8]2.[OH-].[Li+]>O1CCCC1>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([OH:15])=[O:14])[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 14731550Methyl 8-(aminomethyl)naphthalene-2-carboxylate

Product 1

HCID 147565638-(Aminomethyl)naphthalene-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 8-aminomethyl-2-naphthoate (0.75 g, 0.0035 mol) in dry tetrahydrofuran (50 mL), cooled to 0° C., was added a solution of lithium hydroxide (0.5M, 5.83 mL). All was stirred at ambient temperature over 20 hours. Another aliquot of lithium hydroxide was added and all was stirred for an additional 20 hours. The solid was collected and the filtrate was evaporated to dryness under reduced pressure. The solids were triturated with diethyl ether to give 8-aminomethyl-2-naphthoic acid (0.67 g, 0.0033 mol, 95%) as a white solid. mp=223°-225° C.; 1H NMR (DMSO) d 8.6 (s, 1H), 8.1-7.9 (m, 1H), 7.8-7.7 (m, 4H), 7.55-7.5 (m, 1H), 7,45-7.35 (m, 2H), 4.2 (s, 2H).

Workup

  1. stirringall was stirred for an additional 20 hours
  2. customThe solid was collected
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe solids were triturated with diethyl ether

Sources & evidence

ORD record
ord-55094b53df5f4597b0e34c960d785126
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

Loading…