Formic Acid → 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde

HRID 1504115Notes

Reaction equation

[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([C:19]#N)[CH:17]=[CH:18][C:4]1=2)[CH3:2].C(O)=[O:22]>[Ni]>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:11])([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH:19]=[O:22])[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile(1.0 g) and Raney nickel(3.0 g) were suspended in formic acid(10 ml), and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was filtered to remove insoluble matter, and the filtrate was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=50:50→20:80). The purified product was condensed under reduced pressure to give the title compound(0.92 g) as a yellowish-white solid (yield=92%).

Workup

filtrationThe reaction mixture was filtered
customto remove insoluble matter
customcondensed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=50:50→20:80)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-1579b0d0bd794b2a8503296cc80c1efd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

Loading…