2-Bromo-2'-nitroacetophenone → 3-[4-(2-Nitro-phenyl)-oxazol-2-yl]-propionic acid methyl ester

HRID 1616626Notes

Reaction equation

HRID 1616626 reaction equation
COC(=O)CCCC1OC=C(C2C=CC=CC=2[N+]([O-])=O)N=1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])=O.[CH3:35][O:36][C:37](=[O:43])[CH2:38][CH2:39][C:40]([NH2:42])=[O:41]>>[CH3:35][O:36][C:37](=[O:43])[CH2:38][CH2:39][C:40]1[O:41][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])[N:42]=1

Participants

4

Reactant 3

HCID 2440252-Bromo-2'-nitroacetophenoneHCID 12550576Methyl 3-carbamoylpropanoateHCID 591677914-[4-(2-Nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Product 1

HCID 591677493-[4-(2-Nitro-phenyl)-oxazol-2-yl]-propionic acid methyl esterYield 36%

Procedure

Using a method similar to the procedure described for the preparation of 4-[4-(2-nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester; reaction of 2-bromo-2′-nitroacetophenone (15.43 g, 63.2 mmol) with succinamic acid methyl ester (14.4 g, 110 mmol) gives 3-[4-(2-nitro-phenyl)-oxazol-2-yl]-propionic acid methyl ester (6.24 g, 36%). MS (ES): (M+1)+ 277.1 m/z.

Sources & evidence

ORD record
ord-b7d54ff192d84bbfafc528d09145f1dd
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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