4-formylnaphthalene-1-carboxylic Acid → 4-[(3-Chloro-4-hydroxybenzoyl)hydrazonomethyl]naphthoic Acid

HRID 1166740Notes

Reaction equation

HRID 1166740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].[CH:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]([OH:27])=[O:26])=[CH:17][CH:16]=1)=O>CS(C)=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][N:8]=[CH:13][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]([OH:27])=[O:26])=[CH:17][CH:16]=1)=[O:6]

Participants

6

Reactant 2

HCID 108996344-formylnaphthalene-1-carboxylic AcidHCID 109542683-Chloro-4-hydroxybenzohydrazide

Product 1

HCID 674838154-[(3-Chloro-4-hydroxybenzoyl)hydrazonomethyl]naphthoic Acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-4-hydroxybenzoic acid hydrazide (1.53 g, 8.23 mmol) in DMSO (20 mL) was added a solution of 4-formylnaphthoic acid (1.65 g, 8.23 mmol) in DMSO (2 mL). After stirring the solution for 16 hr, the reaction was diluted with ethyl acetate (30 mL) and water (30 mL). A precipitate formed. The precipitate was collected, washed with hexane and dried to give the product as a white solid in quantitative yield.

Workup

  1. customA precipitate formed
  2. customThe precipitate was collected
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-e12c462f8b944dcea7db9630324b87f1
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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