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

HRID 2059657노트

반응식

HRID 2059657 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d7427f6b928d41fcbcb6ee02a0fb9346
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278302B2

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