2-Fluoroaniline → Methyl 4-amino-3-fluoro-2-((2-fluorophenyl)amino)-5-nitrobenzoate

HRID 31972

Reaktionsgleichung

Reaktionsgleichung von HRID 31972
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1F.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[F:17]

Komponenten

4

Edukt 2

HCID 95842-FluoroanilineHCID 2759749Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester

Produkt 1

HCID 71651125Methyl 4-amino-3-fluoro-2-((2-fluorophenyl)amino)-5-nitrobenzoateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

4-Amino-2,3-difluoro-5-nitro-benzoic acid methyl ester 4 (1.50 g, 6.46 mmol) is suspended in xylenes (7.5 mL) and 2-fluoro-phenylamine (6.24 mL, 64.6 mmol) is added. The reaction mixture is stirred at 140° C. under N2. After stirring for 6 days, the reaction is complete. The reaction mixture is cooled to room temperature and diluted with methylene chloride and filtered through a silica gel plug eluting with methylene chloride (1L) to give an orange filtrate. The filtrate is concentrated to dryness and then triturated with diethyl ether to yield a bright yellow solid. The trituration is repeated. The yellow solid is collected to yield 1.08 g (52%) of the pure desired product. MS APCI (−) m/z 322 (M−1) detected.

Aufarbeitung

  1. stirringAfter stirring for 6 days
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationfiltered through a silica gel plug
  4. washeluting with methylene chloride (1L)
  5. customto give an orange filtrate
  6. concentrationThe filtrate is concentrated to dryness
  7. customtriturated with diethyl ether
  8. customto yield a bright yellow solid
  9. customThe yellow solid is collected

Quellen und Nachweise

ORD-Eintrag
ord-a218f4c9703d410ba27d4755e5577c3e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425637B2

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