2,5-Dichloronitrobenzene → HCID 15229161, compound

HRID 1198384Notes

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 g) 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 1N 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.

Workup

customThe reaction was placed in an oil bath
customThe reaction Was then evaporated
customthe residue partitioned between chloroform (75 mL) and 1N 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-ea07649e5c2f43f9bfc416d5b0d5d56b
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281590

Reaction notes

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