4-Nitroanthranilic acid → 2-Amino-4-nitrobenzoyl chloride

HRID 889437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889437
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>>[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Komponenten

3

Edukt 2

HCID 120764-Nitroanthranilic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 214891672-Amino-4-nitrobenzoyl chlorideAusbeute 119,8 %

Versuchsvorschrift

2-Amino-4-nitrobenzoic acid (15 g, 82 mmol) was refluxed with sulfurous dichloride (40 mL, 82 mmol) for 2.5 hours. The reaction mixture was cooled to room temperature and concentrated to give Intermediate 69A (19.7 g, 119%) as a brown oil. HPLC: Rt=2.323 (as methyl ester) min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm.). MS (ES): m/z=197 (as methyl ester) [M+H]+.

Aufarbeitung

  1. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af787e895f6b4bf089469efea35f5a1b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252795B2

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