That wouldn't by any chance happen to be a 4-methylpropiophenone would it? ;) Something that crossed my mind too, but I don't know of any simple ways to reduce the oxime to the amine without affecting the ketone, or at least causing dimerisation due to heat. I'm guessing you do though, and I'm very much looking forward to seeing the results.
Anyway, as to references, the first thing that came into my mind was an old post by Assholium, now archived at https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cb-new.txt (https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cb-new.txt)
, claiming an average 65-70% yield in the articles cited. Here is the link to the Orgsyn article mentioned: http://www.orgsyn.org/orgsyn/default.asp?formgroup=base_form_group&dbname=orgsyn (http://www.orgsyn.org/orgsyn/default.asp?formgroup=base_form_group&dbname=orgsyn)
; although sodium nitrate is used, the generated methyl nitrite isn't actually used in situ, but it's a start I suppose. If I can get access to the JACS articles I'll try and post them. I'm not sure if such old documents are available online, but I did manage to retrieve a 1952 J. Org. Chem. article online a couple of days ago.
Post 402025 (https://www.thevespiary.org/talk/index.php?topic=8149.msg40202500#msg40202500)
(Rhodium: "Ye olde Benzedrine", Stimulants)
Here is a nice method for the selective formation of either alpha-oximinoketones or 1,2-diketones from ketones, with no alkyl nitrites required:
A Practical and User-Friendly Method for the Selenium-Free One-Step Preparation of 1,2-Diketones and their Monoxime Analogs
Matthias A. Oberli, Matthias Nagel, Christophe Weymuth, Hans-Jürgen Hansena
Synlett 2004 [The DOI given in the paper does not work, and the pages aren't numbered]
Abstract
Treatment of alpha-methylene ketones with excess sodium nitrite and aqueous HCl in THF at reduced temperatures provides an effective tool for the preparation of a variety of 1,2-diketones. The diastereoselective synthesis of the corresponding (Z)-1,2-dione monoximes could be accomplished under similar conditions, but by using only one equivalent of nitrosating reagent.
General Procedure for the Prearation of 1,2-Diketones and 1,2-Dione Monoximes
A suspension of the starting ketone (50 mmol) and NaNO2 (10.35 g, 150 mmol) in THF (100 mL) was cooled to 0 °C. To this mixture, concd HCl (65 mL) was added in such a way that the temperature did not exceed 10 °C. In order to avoid the evolution of nitrous gases the acid was added via cannula that was immerged into the reaction mixture. After the addition the cooling bath was removed and the suspension turned dark yellow. The progress of the reaction was monitored by GC. After the starting material had vanished (0.1–12 h) the reaction mixture containing the crude 1,2-diketone was poured into a separatory funnel containing crushed ice (200 g) and Et2O (100 mL). The organic layer was separated, and the aqueous phase extracted with Et2O (3× 100 mL). The combined organic layers were washed with a sat. aq solution of NaHCO3 (100 mL) and with brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by filtration over a pad of silica gel (5:1) using hexane–EtOAc (50:1) as eluent. The corresponding 1,2-dione monoximes were prepared accordingly by using only 3.45 g (50 mmol) of NaNO2 and 25 mL of concd HCl. The crude product was purified either by filtration over a pad of silica gel (5:1) using hexane–EtOAc (50:1) as eluent or by crystallization from hexane–EtOAc.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)