Hydrochloric Acid → 4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}naphthalene-1-carboxylic Acid

HRID 348629Notes

Reaction equation

HRID 348629 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][N:16]([CH2:23][C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)[CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[NH:19]1[CH:20]=[CH:21][N:22]=[C:18]1[CH2:17][N:16]([CH2:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1)[CH2:23][C:24]1[NH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669413384-{[bis(1H-imidazol-2-ylmethyl)amino]methyl)naphthalene-1-carboxylic acid methyl ester

Product 1

HCID 210844614-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}naphthalene-1-carboxylic AcidYield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (675 mg) obtained in Example 36-3 was added with methanol (7.0 ml) and a 1 mol/l sodium hydroxide (7.0 ml), followed by stirring for 1 hour. After completion of the reaction, 1 mol/l hydrochloric acid (8.0 ml) was added to adjust the solution to pH 4. Then, the solvent was distilled off and the residue was washed with methanol, followed by drying. Consequently, the subject compound (677 mg) was obtained as a white solid.

Workup

  1. additionwas added
  2. distillationThen, the solvent was distilled off
  3. washthe residue was washed with methanol
  4. customby drying

Sources & evidence

ORD record
ord-c4553b524fea4f88ab3c073c3a13fde2
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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