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

HRID 621852Notes

Reaction equation

HRID 621852 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-f6e758ff977049fcb125dade6936e760
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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