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

HRID 562524

反応式

HRID 562524 の反応式
[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]

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 120695-Nitroisophthalic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-43d77f5ddfbd4af4bf35a78f513804a3
出典データセット
uspto-grants-2011_11
特許番号
US08067362B2

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