4-Chloro-3-nitrobenzoic acid → 4-chloro-N-methyl-3-nitrobenzamide

HRID 1532661Notes

Reaction equation

HRID 1532661 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].Cl.CN.[CH2:21]([N:23](CC)CC)C>CN(C)C=O>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:23][CH3:21])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 73204-Chloro-3-nitrobenzoic acidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 7992864-chloro-N-methyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (0.65 ml) was added to a solution containing 4-chloro-3-nitrobenzoic acid (1.50 g) in N,N-dimethylformamide (15 ml) and stirred for 30 minutes at room temperature. Methylamine hydrochloride (1.21 g) and triethylamine (3.11 ml) were added to the reaction mixture. After being stirred for 1 hour at room temperature, the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with water, 1N sodium hydroxide aqueous solution, 1N hydrochloric acid aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The yellow solid residue was purified by silica gel column chromatography (silica gel 10 g, chloroform:methanol=1:0-10:1), thereby yielding the entitled compound (0.97 g) as pale yellow solid.

Workup

  1. stirringAfter being stirred for 1 hour at room temperature
  2. concentrationthe reaction mixture was concentrated
  3. additionThe residue, with ethyl acetate added
  4. washwas washed with water, 1N sodium hydroxide aqueous solution, 1N hydrochloric acid aqueous solution and saturated brine successively
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated
  7. customThe yellow solid residue was purified by silica gel column chromatography (silica gel 10 g, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-280327f4c0044d9bbcecb213aea13b42
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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