3-Chloro-4-hydroxybenzohydrazide → HCID 54275027, compound

HRID 1166726Notes

Reaction equation

HRID 1166726 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].[F:13][C:14]([F:40])([F:39])[C:15]1[CH:16]=[C:17]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=O)=[CH:22][CH:21]=1>CS(C)=O.C(O)(=O)C.C(OCC)(=O)C>[F:13][C:14]([F:39])([F:40])[C:15]1[CH:16]=[C:17]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=[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:22][CH:21]=1

Participants

6

Reactant 2

HCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 22999193HCID 22999193, compound

Product 1

HCID 54275027HCID 54275027, 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-(3,5-bis-trifluoromethylbenzyloxy)-1-naphthaldehyde (440 mg, 1.1 mmol) 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 under 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 under vacuo

Sources & evidence

ORD record
ord-846363a180db4420b997f7e6f4435425
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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