Phenylacetylene → 1-Phenyl-2-(3-(isopropyl)amino-4-nitrophenyl)acetylene

HRID 250729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250729
[CH:1]([NH:4][C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])([CH3:3])[CH3:2].[C:15]1([C:21]#[CH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:15]1([C:21]#[C:22][C:9]2[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[CH:10]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 2

HCID 10821PhenylacetyleneHCID 249029775-Bromo-N-isopropyl-2-nitroaniline

Produkt 1

HCID 668688151-Phenyl-2-(3-(isopropyl)amino-4-nitrophenyl)acetyleneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Bubble nitrogen through a mixture of N-[isopropyl]2-nitro-5-bromoaniline (0.34 g, 1.31 mmol), phenylacetylene (0.20 g, 1.96 mmol), palladium(II) acetate (7.3 mg, 0.033 mmol) and triphenylphosphine (17 mg, 0.065 mmol) in triethylamine (5 ml) for 3 minutes, then heat at reflux for 1 hour. Cool to room temperature and concentrate under reduced pressure. Partition the residue between ethyl acetate and saturated aqueous sodium chloride, dry the organic phase over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 9:1 hexane:ethyl acetate to provide the desired compound as a red solid (0.31 g, 85%).

Aufarbeitung

  1. customBubble nitrogen
  2. temperatureheat
  3. temperatureat reflux for 1 hour
  4. concentrationconcentrate under reduced pressure
  5. customPartition the residue between ethyl acetate and saturated aqueous sodium chloride
  6. dry with materialdry the organic phase over sodium sulfate
  7. concentrationconcentrate under reduced pressure
  8. washeluting with 9:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-8b08fa5269ea49c69d026769159d5a0f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863310B2

Notizen zur Reaktion

Wird geladen…