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

HRID 1094982노트

반응식

HRID 1094982 반응식
[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]

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 8082Piperidine2회HCID 4311764Sodium borohydrideHCID 11446896Methyl 5-amino-2-nitrobenzoateHCID 61306566Methyl 2-amino-5-(piperidin-1-yl)benzoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-baa5f130cf4f4c78a16743c1311d3d10
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134015B2

반응 노트

불러오는 중…