Dimethylformamide → HCID 59621122, compound

HRID 2061323Notes

Reaction equation

HRID 2061323 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:14](Cl)(=O)[C:15](Cl)=O.CN(C)[CH:22]=[O:23]>ClCCl>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([C:15]1[CH:14]=[CH:4][C:3]([O:23][CH3:22])=[CH:2][CH:1]=1)=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 59621122HCID 59621122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-methyl-5-nitro-benzoic acid (50 g) in dichloromethane (330 mL) is added oxalyl chloride (25.5 mL) followed by dimethylformamide (0.5 mL). The reaction mixture is stirred at ambient temperature for 14 h, then filtered and separated from all volatile constituents in a rotary evaporator. The residue is dissolved in dichloromethane (100 mL), the resulting solution is cooled to −5° C., and anisole (31 mL) is added. Then aluminum trichloride (37.5 g) is added batchwise so that the temperature maintains below 5° C. The solution is stirred for another 1 h at 1 to 5° C. and then poured onto crushed ice. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with aqueous hydrochloric acid (1 mol/L), twice with aqueous sodium hydroxide solution (1 mol/L) and with brine. The organic phase is dried (sodium sulphate), the solvent is removed and the residue is recrystallised from ethanol.

Workup

  1. filtrationfiltered
  2. customseparated from all volatile constituents in a rotary evaporator
  3. dissolutionThe residue is dissolved in dichloromethane (100 mL)
  4. temperaturethe resulting solution is cooled to −5° C.
  5. additionanisole (31 mL) is added
  6. additionThen aluminum trichloride (37.5 g) is added batchwise so that the temperature
  7. custommaintains below 5° C
  8. stirringThe solution is stirred for another 1 h at 1 to 5° C.
  9. additionpoured
  10. customonto crushed ice
  11. customThe organic phase is separated
  12. extractionthe aqueous phase is extracted with dichloromethane
  13. washThe combined organic phases are washed with aqueous hydrochloric acid (1 mol/L), twice with aqueous sodium hydroxide solution (1 mol/L) and with brine
  14. dry with materialThe organic phase is dried (sodium sulphate)
  15. customthe solvent is removed
  16. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-d4b9cc2dc09a4d6398338f4e2d2ac13e
Source dataset
uspto-grants-2012_10
Patent number
US08283326B2

Reaction notes

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