4-Hydroxy-1-naphthaldehyde → HCID 136065557, compound

HRID 1166725Notes

Reaction equation

HRID 1166725 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].[OH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=O)=[CH:16][CH:15]=1>CS(C)=O.C(O)(=O)C.C(OCC)(=O)C>[OH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=[N:8][NH:7][C:5](=[O:6])[C:4]2[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 3442904-Hydroxy-1-naphthaldehydeHCID 109542683-Chloro-4-hydroxybenzohydrazide

Product 1

HCID 136065557HCID 136065557, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-4-hydroxybenzoic acid hydrazide (200 mg, 1.1 mmol) in DMSO (2 ml) was added 4-hydroxynaphthaldehyde and a catalytic amount of glacial acetic acid (5 drops). The reaction was stirred overnight under nitrogen and diluted with ethyl acetate. The solution was washed with saturated sodium bicarbonate, water, brine, and dried over MgSO4. The organic volume was concentrated in vacuo to give the crude product. The product was purified by silica gel column chromatography using CH2Cl2/MeOH as the mobile phase.

Workup

  1. washThe solution was washed with saturated sodium bicarbonate, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationThe organic volume was concentrated in vacuo

Sources & evidence

ORD record
ord-9718f8a24b3c43b9a0f445e19b898d7b
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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