[clark26]

Hi..

What protection group can you use when you have to protect o-aminoaniline against grignard and subsequent acid (HCl and HBr)? I'm really lost.

[OrgoTutor]

Hi clark26, this may be too late, but if not, could you elaborate on what kind of reaction you're trying to accomplish? For instance, is this part of multi-step synthesis problem? I'm not familiar with any reactions of o-aminoaniline (even if it were protected) and a grignard.

[winkler]

Hi..

What protection group can you use when you have to protect o-aminoaniline against grignard and subsequent acid (HCl and HBr)? I'm really lost.

U should try acilation of aniline with CH3COCl.Thats good protective group.

[OrgoTutor]

U should try acilation of aniline with CH3COCl.Thats good protective group.

Unfortunately, acylation wouldn't protect against a grignard--acylation would create an amide with a proton on the nitrogen that's acidic enough to be deprotonated by the (strongly basic) grignard--or the grignard would attack the carbonyl of the newly formed amide.

Acylation would, however, protect for a Friedel-Crafts acylation or alkylation.

I still don't think there was going to be a reaction take place in any case.

[Kran]

Weird idea here, can`t you react o-aminoaniline with excess glyoxal? It could make a bridge. Not sure if this compount can be isolated, but if it can, you should be able to do your grignard reaction.

[Arctic-Nation]

Imines aren't exactly impervious to Grignard reagents.

Converting the amines to amides, then using 3+ equivalents of Grignard reagent might work, if the Grignard isn't a costly product.