Methyl p-toluenesulfonate → Methyl 2-amino-6-nitrobenzoate

HRID 231571

反応式

HRID 231571 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

参加物

5

反応物 3

HCID 6645Methyl p-toluenesulfonateHCID 8471TriethylamineHCID 957952-Amino-6-nitro-benzoic acid

生成物 1

HCID 596477Methyl 2-amino-6-nitrobenzoate収率 59.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-amino-6-nitrobenzoic acid (11.9 g, 65.3 mmol), methyl p-toluenesulfonate (15.1 g, 81.1 mmol) and triethylamine (6.60 g, 65.3 mmol) in DMF (170 ml) was stirred under N2 at 60° for 18 hours. After removing DMF at 60° and 0.2 mm pressure, the residue was dissolved in ETOAc and washed with a saturated solution of NaHCO3 followed by a saturated aqueous solution of NaCl. The EtOAc extract was dried (Na2SO4), filtered and concentrated under reduced pressure. Flash chromatography over silica gel and elution with 50% toluene-50% CHCl3 gave methyl 2-amino-6-nitrobenzoate (7.6 g, 59.4%), m.p. 105-107°.

後処理

  1. customAfter removing DMF at 60°
  2. dissolution0.2 mm pressure, the residue was dissolved in ETOAc
  3. washwashed with a saturated solution of NaHCO3
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washFlash chromatography over silica gel and elution with 50% toluene-50% CHCl3

出典と根拠

ORDレコード
ord-130a99a50eca4b8ea8c5ae42eb660d16
出典データセット
uspto-grants-1989_07
特許番号
US04847294

関連ノート

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