tert-Butoxy bis(dimethylamino)methane → (E)-2-(2-(dimethylamino)vinyl)-4-nitrobenzonitrile

HRID 735490Notes

Reaction equation

[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O[CH:18](N(C)C)[N:19]([CH3:21])[CH3:20])(C)(C)C>CN(C=O)C>[CH3:18][N:19]([CH3:21])/[CH:20]=[CH:1]/[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-methyl-4-nitrobenzonitrile (5.0 g, 31 mmol) and tert-butoxybis(dimethylamino)methane (12.2 mL, 59 mmol) in dry DMF (8 mL) was stirred at 70° C. for 2 h under N2. After cooling to rt, DMF was removed in vacuo and the crude product was triturated with hexanes/EtOAc (5:1). The solid was collected by filtration and washed with hexane to give Intermediate 1A (6.5 g, 97%) as black solid. 1H NMR (400 MHz, CDCl3) δ 2.97 (s, 6H), 5.36 (d, J=13.2 Hz, 1H), 7.16 (d, J=13.6 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.60 (m, 1H), 8.11 (d, J=1.8 Hz, 1H).

Workup

temperatureAfter cooling to rt
customDMF was removed in vacuo
customthe crude product was triturated with hexanes/EtOAc (5:1)
filtrationThe solid was collected by filtration
washwashed with hexane

Sources & evidence

ORD record: ord-1f3a5a3d190e4250ae1f8c7628cb98e9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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