Sulfuric Acid → 2-Nitro-5-propylamino-benzoic acid methyl ester

HRID 1094982ノート

反応式

HRID 1094982 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].CO[C:17](=O)[C:18]1C=C(N2CCCCC2)C=C[C:19]=1N.N1CCCCC1.S(=O)(=O)(O)O.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH:10][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 8082Piperidine2 回HCID 4311764Sodium borohydrideHCID 11446896Methyl 5-amino-2-nitrobenzoateHCID 61306566Methyl 2-amino-5-(piperidin-1-yl)benzoate

生成物 1

HCID 666375222-Nitro-5-propylamino-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

5-Amino-2-nitro-benzoic acid methyl ester (compound A′) (800 mg) was dissolved in dry THF (15 ml). Propionaldehyde (compound D) (870 μl) dissolved in a mixed liquid composed of 3 M sulfuric acid (4 ml) and THF (1 ml) was added to the solution at room temperature. Subsequently, sodium borohydride (231 mg) was added thereto at 0° C., and the mixture was stirred at room temperature for 3 hr. Thereafter, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-nitro-5-propylamino-benzoic acid methyl ester as a useful intermediate (608 mg, yield 63%).

後処理

  1. additionwas added to the solution at room temperature
  2. distillationThereafter, distilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-baa5f130cf4f4c78a16743c1311d3d10
出典データセット
uspto-grants-2012_03
特許番号
US08134015B2

反応ノート

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