2,5-Dichloronitrobenzene → HCID 15229161, compound

HRID 1646488Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].Cl[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([O:3][C:4]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=2[CH:6]=[O:7])=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium hydride (0.66 q) Was added in portions to a stirred solution of 3.90 g of 2-hydroxy-4-methoxybenzaldehyde in N,N'-dimethylformamide (70 mL) under nitrogen. To the resulting milky, green mixture was added 1,4-dichloro-2-nitrobenzene (4.47 g). The reaction was placed in an oil bath and stirred at 90° C. for 16 hours. The reaction was then evaporated and the residue partitioned between chloroform (75 mL) and 1 N NaOH (50 mL). The layers were separated and the aqueous layer was extracted with chloroform (75 mL). The chloroform extracts were combined and washed with water (75 mL) and brine (75 mL), dried over magnesium sulfate, and evaporated in vacuo. The orange solid was recrystallized from ethyl acetate/iso-propyl ether to yield 3.86 g (53.9%) of product as light yellow, shiny crystals. Melting Point: 130°-131° C.

Workup

customThe reaction was placed in an oil bath
customThe reaction was then evaporated
customthe residue partitioned between chloroform (75 mL) and 1 N NaOH (50 mL)
customThe layers were separated
extractionthe aqueous layer was extracted with chloroform (75 mL)
washwashed with water (75 mL) and brine (75 mL)
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe orange solid was recrystallized from ethyl acetate/iso-propyl ether

Sources & evidence

ORD record: ord-2b4b2345251043e7917e00ce5d75c2fc
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180720

Reaction notes

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