Methylamine → N-Methyl-5-nitro-isophthalamic acid ethyl ester

HRID 2059657Notes

Reaction equation

HRID 2059657 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([C:16](Cl)=[O:17])[CH:8]=1)[CH3:4]>C1COCC1>[CH2:3]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([C:16]([NH:2][CH3:1])=[O:17])[CH:8]=1)[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 3023043Ethyl 3-(chlorocarbonyl)-5-nitrobenzoate

Product 1

HCID 47099901N-Methyl-5-nitro-isophthalamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 2M solution of methylamine in THF (256 ml) at −20° C. was added a pre-cooled solution of 3-chlorocarbonyl-5-nitro-benzoic acid ethyl ester (60 g) in THF (500 ml) dropwise. This was stirred for 20 min and then filtered. The filtrate was concentrated in vacuum and the solid recrystallised from diethyl ether to give the title compound (22.5 g) as a solid. An oxalyl chloride solution in DCM (63 ml, 2M), was added with DMF (5 ml). The reaction was stirred for 2 h and then concentrated in vacuum. The residue was triturated with toluene and again concentrated in vacuum leaving the title compound (60 g). Rt=1.53 min (method D).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuum
  3. customthe solid recrystallised from diethyl ether

Sources & evidence

ORD record
ord-d7427f6b928d41fcbcb6ee02a0fb9346
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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