5-Chloro-salicylaldehyde → HCID 19074353, compound

HRID 1464439Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[H-].[Na+].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

Conditions

Temperature: 63 °C

Procedure

To a stirred solution of 5-chlorosalicylaldehyde (4.00 g) in N,N-dimethylformamide (40 mL) under nitrogen was added sodium hydride in portions (0.64 g). To the resulting reddish solution was added a solution of 1-fluoro-2-nitrobenzene (3.50 g) in N,N-dimethylformamide (10 mL) in one lot. The reaction was then stirred at 63° C. under nitrogen for 24 hours. The reaction was evaporated under vacuum, and the residue was partitioned between chloroform and 1 N NaOH. The layers were separated, and the aqueous layer was extracted once more with chloroform. The combined chloroform extracts were washed with 1 N NaOH, water, 1 N HCl, water, and brine, dried over magnesium sulfate, and evaporated under vacuum. The residue was crystallized from cyclohexane to yield the title compound as a light yellow solid. Mp: 103°-105° C.

Workup

customThe reaction was evaporated under vacuum
customthe residue was partitioned between chloroform and 1 N NaOH
customThe layers were separated
extractionthe aqueous layer was extracted once more with chloroform
washThe combined chloroform extracts were washed with 1 N NaOH, water, 1 N HCl, water, and brine
dry with materialdried over magnesium sulfate
customevaporated under vacuum
customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record: ord-adfe915ccbe144a89c1a4687bd13a403
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304644

Reaction notes

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