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

HRID 1991190ノート

反応式

HRID 1991190 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-50869fe8e3df434ab350bf602623828f
出典データセット
uspto-grants-2010_01
特許番号
US07645784B2

反応ノート

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