1-Hydroxybenzotriazole → 6-Hydroxynaphthalene-2-carboxamide

HRID 907079Notes

Reaction equation

HRID 907079 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.Cl.C[N:17](C)CCCN=C=NCC.O[N:28]1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C)C=O>[NH3:17].[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH2:28])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 855576-Hydroxy-2-naphthoic acidHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 2

HCID 222AmmoniaHCID 143234946-Hydroxynaphthalene-2-carboxamideYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-2-napthoic acid (1.88 g, 9.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.11 g, 10.98 mmol), 1-hydroxybenzotriazole (1.48 g, 10.98 mmol) and ammonium carbonate (4.80 g, 49.95 mmol) in N,N-dimethylformamide (70 ml) was left to stir at room temperature under a nitrogen atmosphere for 3 days. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (6×50 ml). The combined organic extracts were washed with water (25 ml), saturated aqueous sodium chloride (25 ml), dried (sodium sulfate) and the solvent removed in vacuo. The solid was absorbed onto silica gel and purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.880 ammonia (95:5:0.5 changing to 90:10:1) to give the title compound as a pale yellow solid (1.1 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (6×50 ml)
  3. washThe combined organic extracts were washed with water (25 ml), saturated aqueous sodium chloride (25 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe solid was absorbed onto silica gel
  7. custompurified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b689c303ad954dc4850907a387bc34c7
Source dataset
uspto-grants-2011_09
Patent number
US08013019B2

Reaction notes

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