Sodium Hydroxide → methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate

HRID 1052360

Reaktionsgleichung

Reaktionsgleichung von HRID 1052360
[Br:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[OH-].[Na+].[OH-].[NH4+:14].[Cl-].[NH4+].Cl[O-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:14][N:4]1[CH:5]=[CH:6][C:2]([Br:1])=[C:3]1[C:7]([O:9][CH3:10])=[O:8]

Komponenten

7

Edukt 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 23665760Sodium HypochloriteHCID 44189804methyl 3-bromo-1H-pyrrole-2-carboxylate

Produkt 1

HCID 70979762methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylateAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21218Trioctylmethylammonium chlorideKatalysator

Versuchsvorschrift

Methyl 3-bromo-1H-pyrrole-2-carboxylate (1.74 g, 8.53 mmol) was treated with an aqueous solution of sodium hydroxide (32%, 25 mL, 172.3 mmol), ammonium hydroxide solution (8M, 8 mL, 63.5 mmol), ammonium chloride (2.74 g, 51.2 mmol), aliquat 336 (312 μl, 0.68 mmol) and a 10% aqueous solution of sodium hypochlorite (10%, 56 mL, 75.4 mmol) according to the method of Preparation 4c to give 600 mg (23% yield) of the title product. Purity 70%.

Quellen und Nachweise

ORD-Eintrag
ord-b9ded6cbb2544cabb69d2a609c456219
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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