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

HRID 2059657ノート

反応式

HRID 2059657 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d7427f6b928d41fcbcb6ee02a0fb9346
出典データセット
uspto-grants-2012_10
特許番号
US08278302B2

反応ノート

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