3-Chloro-4-hydroxybenzohydrazide → {4-[(3-Chloro-4-hydroxy-benzoyl)hydrazonomethyl]naphth-1-yloxy}acetic acid

HRID 1166730Notes

Reaction equation

HRID 1166730 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]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:17][CH:16]=1)=O>CS(C)=O.C(O)(=O)C.C(OCC)(=O)C>[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]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:17][CH:16]=1)=[O:6]

Participants

6

Reactant 2

HCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 54232122(4-Formylnaphth-1-yloxy) acetic acid

Product 1

HCID 70030032{4-[(3-Chloro-4-hydroxy-benzoyl)hydrazonomethyl]naphth-1-yloxy}acetic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-4-hydroxybenzoic acid hydrazide (2 g, 10.7 mmol) in DMSO (20 mL) was added the above (4-formylnaphth-1-yloxy) acetic acid (3 g, 13 mmol) and a catalytic amount of acetic acid (10 drops). The solution was stirred overnight and diluted with ethyl acetate. The solution was washed with water (3×), brine, and dried over MgSO4. The volume was reduced to approximately 100 mL and placed in an ice-bath. The resulting solid was filtered and washed with cold ethyl acetate to afford {4-[(3-chloro-4-hydroxy-benzoyl)hydrazonomethyl]naphth-1-yloxy}acetic acid.

Workup

  1. washThe solution was washed with water (3×), brine
  2. dry with materialdried over MgSO4
  3. customplaced in an ice-bath
  4. filtrationThe resulting solid was filtered
  5. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-473a12670e98420d8aab400824674634
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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