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

HRID 1991190노트

반응식

HRID 1991190 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50869fe8e3df434ab350bf602623828f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645784B2

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