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

HRID 1443733Notes

Reaction equation

HRID 1443733 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[CH3:14][O:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][C:20](=[O:22])[NH2:21]>CO>[CH3:14][O:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][C:20]1[O:22][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-:13])=[O:12])[N:21]=1

Participants

4

Reactant 2

HCID 2440252-Bromo-2'-nitroacetophenoneHCID 11708070Methyl 4-aminocarbonylbutyrate

Product 1

HCID 591677914-[4-(2-Nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-bromo-2′-nitroacetophenone (10.4 g, 42.6 mmol) with 4-carbamoyl-butyric acid methyl ester (12.2 g, 84.1 mmol) and heat the neat mixture in a sealed vessel at 120-150° C. for about 4-6 h. Cool the mixture, transfer to a round bottom flask with methanol and concentrate. Partition the residue between water and EtOAc. Dry the combined EtOAc extracts over Na2SO4 and concentrate. Initial chromatography over silica gel (EtOAc/CH2Cl2) followed by a second chromatography over silica gel (Hex/EtOAc) allowed for recovery of 4-[4-(2-nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester (3.05 g, 25%). MS (ES): (M+1)+ 291.1, 292.2 m/z.

Workup

  1. concentrationconcentrate
  2. customPartition the residue between water and EtOAc
  3. dry with materialDry the combined EtOAc
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-1a8d6a95ae4f405db48f18d06aca4562
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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