Sulfuric Acid → HCID 86723684, Verbindung

HRID 577446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577446
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].CN(C(O[N:21]1N=N[C:23]2C=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.COC(OC)CN.OS(O)(=O)=O.[OH-].[Na+]>S1(CCCC1)(=O)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:11][CH3:12])[C:6](=[O:8])[NH:21][CH:22]=[CH:23]2

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 5984364-Fluoro-3-methoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 86723684HCID 86723684, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31347SulfolaneLösungsmittel

Versuchsvorschrift

A solution of 4-fluoro-3-methoxybenzoic acid (1.30 g, 7.64 mmol) and TEA (1.25 mL, 8.97 mmol) in sulfolane (6.0 mL) was treated with HATU (3.25 g, 8.55 mmol). After 10 minutes, aminoacetaldehyde dimethylacetal (0.925 mL, 8.58 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was then treated with conc. H2SO4 (15 mL) and stirred at 60° C. for 2 days. The reaction mixture was poured over ice and brought to pH˜4 with 10M NaOH (˜55 mL). The precipitate was collected by filtration, washed with water, and dried under vacuum to give 6-fluoro-7-methoxyisoquinolin-1(2H)-one (Cpd L, 1.32 g, 89%) as a white powder.

Aufarbeitung

  1. stirringstirred at 60° C. for 2 days
  2. additionThe reaction mixture was poured over ice
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fdb5560e7aab40d19ff9338fd477821a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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