Ethanolamine → 2-(2-Hydroxyethylamino)-3-nitrobenzoic acid

HRID 1991189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1991189
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14]([CH2:16][NH2:17])[OH:15]>C(O)C>[OH:15][CH2:14][CH2:16][NH:17][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 198702-Chloro-3-nitrobenzoic acid

Produkt 1

HCID 111488352-(2-Hydroxyethylamino)-3-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Chloro-3-nitrobenzoic acid (5.0 g, 24.8 mmol) was suspended in ethanol (90 mL) and ethanolamine (4.5 mL, 74.8 mmol) was added. The resulting clear solution was heated at 100° C. for two days. The volatiles were removed under reduced pressure. The residue was treated with water (40 mL) and the mixture was acidified with 1M hydrochloric acid to pH 2. A yellow precipitate formed was collected by filtration and washed with water to yield 2-(2-hydroxyethylamino)-3-nitrobenzoic acid, 5.14 g (92%). MS (ESI) m/z 225 [M−H]. 1H NMR (400 MHz, CD3OD) δ ppm 3.04 (t, J=5.31 Hz, 2H), 3.69 (t, J=5.31 Hz, 2H), 6.71 (t, J=7.96 Hz, 1H), 7.93 (dd, J=8.21, 1.64 Hz, 1H), 8.13 (dd, J=7.71, 1.64 Hz, 1H).

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was treated with water (40 mL)
  3. customA yellow precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-709dfe048bf04c9188210331d1c321d9
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645784B2

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