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

HRID 1991189Notes

Reaction equation

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]

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-709dfe048bf04c9188210331d1c321d9
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645784B2

Reaction notes

Loading…