Water → Methyl 2-chloro-3-nitrobenzoate

HRID 567251Notes

Reaction equation

HRID 567251 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].IC.[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-nitrobenzoic acid (20.16 g, 100.0 mM), iodomethane (15.6 g, 110 mM), and potassium carbonate (15.0 g, 108.5 mM) in 100 mL DMF was stirred at room temperature for 48 hours. The mixture was poured into 1.5 liters of H2O. The resultant precipitate was collected by 20.0 g (93%) of methyl 2-chloro-3-nitrobenzoate as a white solid. 1H NMR (CDCl3) δ 8.42 (dd, 1H, J=1 and 8 Hz), 8.18 (dd, 1H, J=1 and 8 Hz), 7.43 (t, 1H, J=8 Hz), and 3.9 (s, 3H). IR (KBr, cm−1) 1743, 1719, 1595, 1540, 1532, 1433, 1357, 1300, and 730. MS (FD) m/e 215, 216.

Workup

  1. customThe resultant precipitate was collected by 20.0 g (93%) of methyl 2-chloro-3-nitrobenzoate as a white solid

Sources & evidence

ORD record
ord-f0657a8d90184118b3124d44080e9c61
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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