Dicyclohexylamine → HCID 178425877, Verbindung

HRID 2357514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357514
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][N:6]=[CH:5]2.B([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:19]([OH:21])=[O:20])(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1.C1(NC2CCCCC2)CCCCC1.[OH-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(O)CCC>[OH:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)[CH:5]=[N:6][N:7]=1

Komponenten

9

Edukt 5

HCID 7582DicyclohexylamineHCID 14798Sodium HydroxideHCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 189801423-Borono-4-methylbenzoic acidHCID 178518904HCID 178518904, Verbindung

Produkt 1

HCID 178425877HCID 178425877, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A 10 mL round bottom flask was charged with 6-chlorophthalazin-1-ol (0.35 g, 1.94 mmol), 3-borono-4-methylbenzoic acid (0.42 g, 2.3 mmol), Pd2(dba)3 (9 mg, 9.8 μmol), and 2-(dicyclohexylphosphino)-2′-methylbiphenyl (9 mg, 25 μmol). The flask was evacuated and back-filled with nitrogen. Deoxygenated solvents, 1-butanol (2.0 mL), water (0.5 mL) and dicyclohexylamine (1.5 mL, 7.8 mmol), were added sequentially. The reaction mixture was then heated at 85° C. under nitrogen with efficient stirring overnight. 6 N NaOH aq. (2 mL, 12 mmol) was added and the reaction mixture was stirred until all solids dissolved. The reaction mixture was allowed to warm to RT and water (10 mL) was added. The reaction mixture was transferred into separatory funnel where the layers were separately collected. The aqueous layer was extracted with DCM (2×10 mL). All the organic solutions were discarded. The aqueous layer was adjusted to about pH 6 using 5N HCl. The resulting fine precipitate was collected by filtration, rinsed thoroughly with water, and air-dried. Oven drying of the solid afforded 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoic acid as a fine off-white powder.

Aufarbeitung

  1. customThe flask was evacuated
  2. additionback-filled with nitrogen
  3. stirringthe reaction mixture was stirred until all solids
  4. dissolutiondissolved
  5. temperatureto warm to RT
  6. customThe reaction mixture was transferred into separatory funnel
  7. customwhere the layers were separately collected
  8. extractionThe aqueous layer was extracted with DCM (2×10 mL)
  9. filtrationThe resulting fine precipitate was collected by filtration
  10. washrinsed thoroughly with water
  11. customair-dried
  12. customOven drying of the solid

Quellen und Nachweise

ORD-Eintrag
ord-8cbe2446d4ee4f9fa4f92cdc70fd0dfe
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759337B2

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