Phenylethanolamine → HCID 14390523, compound

HRID 2072928Notes

Reaction equation

HRID 2072928 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14].C(N(CC)CC)C>C(O)C>[N+:8]([C:7]1[C:2]([NH:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:14])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 14390523HCID 14390523, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (20.0 g, 0.13 mole), 2-amino-1-phenylethanol (20.74 g, 0.15 mole), and triethylamine (17.5 ml, 0.13 mole) in 200 ml of absolute ethanol was heated to reflux for 11/2 hours. The reaction mixture was filtered and evaporated to dryness. The residue was partitioned between water and methylene chloride (2x). The methylene chloride layers were combined and extracted with water. The methylene chloride layers were dried, filtered, and evaporated to a solid (30.8 g, 94.5%). A 2.4-g sample was recrystallized from methanol and water to give a yellow solid, which was collected by filtration, washed with water, and dried under high vacuum overnight to give 1.8 g of the compound, mp 101°-103° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 11/2 hours
  3. filtrationThe reaction mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was partitioned between water and methylene chloride (2x)
  6. extractionextracted with water
  7. dry with materialThe methylene chloride layers were dried
  8. filtrationfiltered
  9. customevaporated to a solid (30.8 g, 94.5%)
  10. customA 2.4-g sample was recrystallized from methanol and water
  11. customto give a yellow solid, which
  12. filtrationwas collected by filtration
  13. washwashed with water
  14. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-76ddc0dd0aa14b5f901e49d45015cb8c
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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