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

HRID 2237244

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

customPurification of the reaction mixture by preparative HPLC

Sources & evidence

ORD record: ord-ff55e94db2b947629a9d0ec2443bce6f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714138B2

Linked notes

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