Methanol → Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

HRID 1991190Notes

Reaction equation

HRID 1991190 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:22]O>>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:22])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 111488352-(2-Hydroxyethylamino)-3-nitrobenzoic acid

Product 1

HCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

Procedure

2-(2-Hydroxyethylamino)-3-nitrobenzoic acid (5.14 g, 22.7 mmol) was dissolved in methanol (200 mL) and concentrated H2SO4 (10 mL) was added. The mixture was heated at reflux for 2.5 h. The solvent was removed at reduced pressure. The residue was treated with water (100 ml) and extracted with ethyl acetate (3×150 mL). The combined organic phase was dried and concentrated. Purification by column chromatography on silica using heptane ethyl acetate 1:1 as an eluent afforded methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate, 3.92 g (72%). MS NISI) m/z 241 [M+H]. 1H NMR (400 MHz, CDCI3) δ ppm 3.12 (t, J=5.10 Hz, 2H), 3.84 (t, J=5.15 Hz, 2H), 3.91 (s, 3H), 6.69 (t, J=7.96 Hz, 1H), 7.95 (dd, J=8.34, 1.52 Hz, 1H), 8.08 (dd, J=7.83, 1.52 Hz, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 h
  3. customThe solvent was removed at reduced pressure
  4. additionThe residue was treated with water (100 ml)
  5. extractionextracted with ethyl acetate (3×150 mL)
  6. customThe combined organic phase was dried
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica

Sources & evidence

ORD record
ord-50869fe8e3df434ab350bf602623828f
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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