2,5-Dichloronitrobenzene → HCID 19102558, compound

HRID 1646485Notes

Reaction equation

HRID 1646485 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[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]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:5]=2[CH:6]=[O:7])=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 24758Sodium hydrideHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 19102558HCID 19102558, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

0.85 g of sodium hydride was added in portions to a stirred solution of 5.00 g of 2-hydroxy-5-methoxybenzaldehyde in 90 mL of N,N'-dimethylformamide under nitrogen. To the resulting milky, green mixture was added 5.74 g of 1,4-dichloro-2-nitrobenzene. The reaction was placed in an oil bath and stirred at 90° C. for 16 hours. The reaction was then evaporated in vacuo, and the residue partitioned between 75 mL of chloroform and 75 mL of 1 N NaOH. The layers were separated and the aqueous layer was extracted With 75 mL of chloroform. The chloroform extracts were combined and washed with water (2×75 mL) and brine (75 mL), dried over magnesium sulfate, and evaporated in vacuo. The semi-solid residue was triturated with diethyl ether. The precipitated product was collected by filtration, washed with ether, and dried in vacuo to yield 5.96 g (64.8%) of product as a yellow solid. Melting Point: 127°-128° C.

Workup

  1. customThe reaction was placed in an oil bath
  2. customThe reaction was then evaporated in vacuo
  3. customthe residue partitioned between 75 mL of chloroform and 75 mL of 1 N NaOH
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted With 75 mL of chloroform
  6. washwashed with water (2×75 mL) and brine (75 mL)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe semi-solid residue was triturated with diethyl ether
  10. filtrationThe precipitated product was collected by filtration
  11. washwashed with ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-4367c003bd6f43188c63417b5b770823
Source dataset
uspto-grants-1993_01
Patent number
US05180720

Reaction notes

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