Sodium Hydroxide → 1-(3-methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid

HRID 644801

Reaktionsgleichung

Reaktionsgleichung von HRID 644801
[CH2:1]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]1[C:14]([O:16]CC)=[O:15])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]1[C:14]([OH:16])=[O:15])[CH2:2][CH:3]([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67183320Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate

Produkt 1

HCID 218807721-(3-methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acidAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate (2.377 g, 9.329 mmol; see step (i) above) was suspended in ethanol (5 mL), then a solution of NaOH (955 mg dissolved in 20 mL of water) was added. The reaction mixture was reduced by half under reduced pressure at 50° C., and then the cooled solution was extracted with ether. The water layer was cooled to 0° C. then conc. HCl was added dropwise with vigorous stirring until pH 2. The white solid material was filtered off, washed with water, dried at 60° C. under reduced pressure for 2 h then left at room temperature overnight. The product was obtained as white solid (2.008 g, 95% yield), m.p. 154-157° C. [Lit.m.p. 154-156° C.].

Aufarbeitung

  1. customwas reduced by half under reduced pressure at 50° C.
  2. extractionthe cooled solution was extracted with ether
  3. additionconc. HCl was added dropwise
  4. filtrationThe white solid material was filtered off
  5. washwashed with water
  6. customdried at 60° C. under reduced pressure for 2 h

Quellen und Nachweise

ORD-Eintrag
ord-fc969097f8e0408eb4811a120b98eae3
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700765B2

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