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

HRID 23147

Reaktionsgleichung

Reaktionsgleichung von HRID 23147
C([O:3][C:4]([C:6]1[N:7]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:17][CH:16]([CH3:18])[CH2:15][CH2:14][N:7]1[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:6]1[C:4]([OH:5])=[O:3]

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 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1-(3-Methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester (1.44 g,) was dissolved in 50 ml of methanol and 25 ml of 20% aqueous NaOH was added. The reaction mixture was stirred at 50° C. for 1.5 h until there was no starting material checked by TLC. The reaction mixture was concentrated to about 20 ml, 200 ml of water was added. The resulting solution was neutralized with 5 M hydrochloric acid to pH 2 and the precipitates formed were collected by filtration, washed with water and dried to give 1-(3-methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid (1.29 g, 99%). 1H NMR (DMSO-d6) δ13.12 (br. s, 1H), 8.27 (d, 1H), 7.26 (d, 1H), 4.36 (t, 2H), 1.59 (dd, 2H), 1.50 (dt, 1H), 0.88 (d, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to about 20 ml, 200 ml of water
  2. additionwas added
  3. customthe precipitates formed
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5ae4b7815f014a428f4a5bf826048932
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849713B2

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