3-Bromo-o-toluidine → 2-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide

HRID 523225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523225
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=O)[O:9]C(=O)[NH:7][C:6]=2[CH:13]=1.[Br:14][C:15]1[C:16]([CH3:22])=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>C1(C)C(C)=CC=CC=1>[NH2:7][C:6]1[CH:13]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[C:10]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([Br:14])[C:16]=1[CH3:22])=[O:9]

Komponenten

4

Edukt 2

HCID 1235383-Bromo-o-toluidineHCID 100581387-Fluoroisatoic anhydride

Produkt 1

HCID 1076239052-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (5.00 g, 27.6 mmol) and 3-bromo-2-methylaniline (5.14 g, 27.6 mmol) in xylene (50 mL) was heated at reflux for 8 h. The cooled mixture was filtered. The collected solid was washed with 3 times with DCM and the combined filtrates were concentrated. The residue was purified by column chromatography on silica gel (330 g), eluting with EtOAc-hexanes (gradient from 0-45%), to give 2-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide (3.65 g, 41% yield). Mass spectrum m/z 323, 325 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ 7.65 (1 H, d, J=8.14 Hz), 7.45-7.57 (3 H, m), 7.14 (1 H, t, J=8.03 Hz), 6.39-6.50 (2 H, m), 5.80 (2 H, br. s.), 2.43 (3 H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. filtrationThe cooled mixture was filtered
  4. washThe collected solid was washed with 3 times with DCM
  5. concentrationthe combined filtrates were concentrated
  6. customThe residue was purified by column chromatography on silica gel (330 g)
  7. washeluting with EtOAc-hexanes (gradient from 0-45%)

Quellen und Nachweise

ORD-Eintrag
ord-9388c606e5994d85b33a841adb9bdcb7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334290B2

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