3-Methyl-2-nitrobenzoic acid → 3-methyl-2-nitrobenzoyl chloride

HRID 2304411Notes

Reaction equation

HRID 2304411 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([Cl:17])=[O:6]

Participants

5

Reactant 2

HCID 215753-Methyl-2-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 2671613-methyl-2-nitrobenzoyl chlorideYield 99.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Methyl-2-nitrobenzoic acid 67 (30.0 g, 166 mmol, 1.0 equiv.) was suspended in CH2Cl2 (150 ml) and the suspension was cooled to 0° C. using an ice bath. Oxalyl chloride (2.0 M in CH2Cl2, 166 ml, 332 mmol, 2.0 equiv.) was added to the stirred reaction mixture through a pressure equalizing dropping funnel over 30 min. DMF (10 drops) was added dropwise. The reaction mixture was allowed to warm up to room temperature. After 30 min., the reaction was concentrated to dryness on a rotary evaporator. The solid material was re-dissolved in CH2Cl2 (200 ml) and was concentrated to dryness on a rotary evaporator to give 3-methyl-2-nitro-benzoylchloride 68 (32.9 g, 99%) as an off white solid.

Workup

  1. customover 30 min
  2. temperatureto warm up to room temperature
  3. concentrationthe reaction was concentrated to dryness on a rotary evaporator
  4. dissolutionThe solid material was re-dissolved in CH2Cl2 (200 ml)
  5. concentrationwas concentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-9eb83df8af634560a707dae9b64c9b9b
Source dataset
uspto-grants-2002_08
Patent number
US06436919B1

Reaction notes

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