1-Amino-2-propanol → 1-[(3-Nitro-2-pyridinyl)amino]-2-propanol

HRID 621852노트

반응식

HRID 621852 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][CH:12]([OH:15])[CH2:13][NH2:14].C(N(CC)CC)C>C(O)C>[N+:8]([C:7]1[C:2]([NH:14][CH2:13][CH:12]([OH:15])[CH3:11])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

참가 물질

5

반응물 3

HCID 41-Amino-2-propanolHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

생성물 1

HCID 156171811-[(3-Nitro-2-pyridinyl)amino]-2-propanol수율 96%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-chloro-3-nitropyridine (10.0 g, 0.063 mole), DL-1-amino-2-propanol (7.1 g, 0.095 mole), and triethylamine (8.75 ml, 0.063 mole) in absolute ethanol was heated at reflux for 11/2 hours. The reaction mixture was evaporated to dryness and the residue was partitioned between water and methylene chloride. The water layer was separated and extracted with methylene chloride (2×). The combined methylene chloride layers were extracted with water and dried over sodium sulfate. The filtrate was evaporated to a yellow oil. The oil was purified on a silica gel column (200 g) eluting first with methylene chloride, followed by 5%, 10%, 25% (500 ml each), and finally 50% ethyl acetate/methylene chloride. The appropriate fractions (TLC using ethyl acetate) were combined and evaporated to an oil. A sample of the oil was dried at 50°-60° C., then at 70° C. for 6 hours to give 11.9 g (96%) of a yellow oil.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue was partitioned between water and methylene chloride
  5. customThe water layer was separated
  6. extractionextracted with methylene chloride (2×)
  7. extractionThe combined methylene chloride layers were extracted with water
  8. dry with materialdried over sodium sulfate
  9. customThe filtrate was evaporated to a yellow oil
  10. customThe oil was purified on a silica gel column (200 g)
  11. washeluting first with methylene chloride
  12. customevaporated to an oil
  13. customA sample of the oil was dried at 50°-60° C.

출처 및 근거

ORD 기록
ord-f6e758ff977049fcb125dade6936e760
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04824951

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