Aniline → (E)-Dimethyl 2-(3-(phenylamino)allylidene)malonate

HRID 2374023

반응식

HRID 2374023 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4](=[CH:9][CH:10]=[CH:11]OC)[C:5]([O:7][CH3:8])=[O:6].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([NH:15]/[CH:11]=[CH:10]/[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:14])[C:5]([O:7][CH3:8])=[O:6])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 6115AnilineHCID 5979922-(3-Methoxy-allylidene)-malonic acid dimethyl ester

생성물 1

HCID 59852887(E)-Dimethyl 2-(3-(phenylamino)allylidene)malonate수율 57.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-(3-methoxyallylidene)malonic acid dimethyl ester (Acros Organics, 200 mg, 1.0 mmol) in THF (2 mL) at rt was added aniline (300 mg, 3.2 mmol) and the reaction mixture was heated at 60° C. for 8.5 h. Purification of the reaction mixture by preparative HPLC provided the desired product (150 mg, 57%) as a yellow solid. 1H NMR (DMSO-d6) δ 10.16 (d, 1H, J=12.7 Hz), 8.06 (t, 1H, J=12.7 Hz), 7.74 (d, 1H, J=12.7 Hz), 7.30 (t, 2H, J=8.7 Hz), 7.16 (d, 2H, J=7.7 Hz), 6.98 (t, 1H, J=7.7 Hz), 6.35 (t, 1H, J=12.1 Hz), 3.69 (s, 3H), 3.65 (s, 3H).

후처리

  1. customPurification of the reaction mixture by preparative HPLC

출처 및 근거

ORD 기록
ord-4af15492bec348c0b925efd0b56dd68c
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459562B2

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