Hydrochloric Acid → Nitrobenzene

HRID 749633Notes

Reaction equation

HRID 749633 reaction equation
N1C=CC=CC=1.Cl[C:8]1[CH:16]=[CH:15][C:11](C(Cl)=O)=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].NC1C=CC=CC=1.Cl>O1CCCC1>[N+:17]([C:9]1[CH:10]=[CH:11][CH:15]=[CH:16][CH:8]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6115AnilineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 7416NitrobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.87 mL (10.8 mmole) of pyridine and 956 mg (4.35 mmoles) of 4-chloro-3-nitrobenzoylchloride were added to a 30 mL tetrahydrofuran solution of 1.0 g (3.6 mmoles) of aniline compound (1B-18) and the mixture was stirred for one hour at room temperature. To the reaction solution was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate, then the solvent was removed under reduced pressure. The residue was slurry washed with ethyl acetate-hexane, yielding 1.41 g (a yield of 85 percent) of nitrobenzene compound (1B-19).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-85a96a601dbd4b0986a5a8d36ea3c4f9
Source dataset
uspto-grants-2008_07
Patent number
US07402696B2

Reaction notes

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