Phosphate → 2-Formyl-6-nitrobenzonitrile

HRID 711813

反応式

HRID 711813 の反応式
COC([O:7][CH3:8])N(C)C.C[C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:11]=1[C:12]#[N:13].P([O-])([O-])([O-])=O>CN(C=O)C.C1COCC1>[CH:8]([C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:11]=1[C:12]#[N:13])=[O:7]

参加物

6

反応物 3

HCID 1061PhosphateHCID 746696-Nitro-2-toluonitrileHCID 78373Dimethylformamide dimethyl acetal

生成物 1

HCID 866574742-Formyl-6-nitrobenzonitrile収率 19%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

1,1-Dimethoxy-N,N-dimethylmethanamine (13.56 mL, 102 mmol) was added to a solution of 2-methyl-6-nitrobenzonitrile (15.0 g, 92.5 mmol) in anhydrous DMF (60 mL) under nitrogen and was heated at 130° C. for 15 h. Ice water (300 mL) was added, and the resultant dark precipitate was collected by filtration and dried under vacuum. Phosphate buffer (pH 7, 350 mL) and then NaIO4 (40 g, 187 mmol) were added to a solution of the dark precipitate in THF (350 mL) and stirred at rt for 3 h. The mixture was extracted with EtOAc, the combined extract was washed with brine and dried with MgSO4. The filtrate was concentrated and the residue was purified by chromatography on silica using the solven gradient hexanes→EtOAc, to give 3.07 g (19%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.15 (t, J=8.4 Hz, 1H), 8.41 (dd, J=1.2, 7.6 Hz, 1H), 8.62 (dd, J=1.2, 8.4 Hz, 1H), 10.25 (s, 1H).

後処理

  1. filtrationthe resultant dark precipitate was collected by filtration
  2. customdried under vacuum
  3. extractionThe mixture was extracted with EtOAc
  4. extractionthe combined extract
  5. washwas washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by chromatography on silica using the solven gradient hexanes→EtOAc

出典と根拠

ORDレコード
ord-0ae6a3f30d2c468ca4577605f5f0987c
出典データセット
uspto-grants-2015_11
特許番号
US09181276B2

関連ノート

読み込み中…