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

HRID 230754

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 afforded the desired product (150 mg, 57%) as a yellow solid. 1H NMR (DMSO-d6) δ 10.16 (d, 1H, J=12.7Hz), 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-518c57da93a047a7929bf4b86a5a0992
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566784B2

Linked notes

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