Phenylethanolamine → HCID 14390523, compound

HRID 2351607Notes

Reaction equation

HRID 2351607 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 (2×). 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 (2×)
  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-ffd74e900eee46e2aa626e1ba11a574c
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

Loading…