4-Chloro-3-nitrobenzoic acid → 4-Chloro-N,N-dimethyl-3-nitrobenzamide

HRID 1532666Notes

Reaction equation

HRID 1532666 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].C(Cl)(=O)C(C)(C)C.Cl.CNC>CN(C)C=O>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:3]([CH3:4])[CH3:1])=[O:14])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 73204-Chloro-3-nitrobenzoic acidHCID 8471Triethylamine2×HCID 10473Dimethylamine, hydrochlorideHCID 62493Pivaloyl chloride

Product 1

HCID 2201034-Chloro-N,N-dimethyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (3.48 ml) was added to a solution containing 4-chloro-3-nitrobenzoic acid (5.04 g) in N,N-dimethylformamide (25 ml) while being cooled with ice, and then pivaloyl chloride (3.08 ml) was added thereto. The mixture was stirred for 15 minutes, and then dimethylamine hydrochloride (2.24 g) and triethylamine (3.83 ml) were added thereto. The reaction mixture was stirred for 15 minutes while being cooled with ice and futher stirred for 14 hours at room temperature, and then concentrated. The residue, with ethyl acetate added thereto, was washed with water, 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (4.85 g) as yellow solid.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringThe reaction mixture was stirred for 15 minutes
  3. temperaturewhile being cooled with ice and futher
  4. stirringstirred for 14 hours at room temperature
  5. concentrationconcentrated
  6. additionThe residue, with ethyl acetate added
  7. washwas washed with water, 1N sodium hydroxide aqueous solution and saturated brine successively
  8. dry with materialdried over sodium sulfate anhydride
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-42029b47f0f04d928778d85c23cd98c6
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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