Dimethylformamide → 3-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acid

HRID 562524

Reaction equation

HRID 562524 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-:3])=[O:2].CN(C)C=O>C1(C)C=CC=CC=1>[C:6]([O:14][C:13](=[O:15])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=1)([CH3:13])([CH3:7])[CH3:5]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 120695-Nitroisophthalic acid

Product 1

HCID 693810873-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acidYield 248.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 5-nitro-isophthalic acid (5.0 g, 23.7 mmol) in dry toluene (100 ml) at 110° C. was added dimethylformamide di-t-butylacetale (3.4 ml, 71 mmol) drop wise over 60 min. Heating was continued for 45 min and the reaction mixture was left at Rt over night. The precipitated starting material was removed by filtration. The filtrate was concentrated to give a yellow oil (7.88 g). This was purified by flash chromatography using EtOAc/Hept 1:2 and EtOAc/Hept 1:2+5% AcOH in two portions to give the title compound in 38% yield (2.38 g)

Workup

  1. temperatureHeating
  2. waitthe reaction mixture was left at Rt over night
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-43d77f5ddfbd4af4bf35a78f513804a3
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Linked notes

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