Triethylamine → HCID 69666330, compound

HRID 1839102Notes

Reaction equation

HRID 1839102 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][C@H:23]([CH2:26][CH3:27])[CH2:24][OH:25]>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][C@H:23]([CH2:26][CH3:27])[CH2:24][OH:25])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27238562-Amino-1-butanol, (-)-HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 69666330HCID 69666330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Crude 4-chloro-3-nitroquinoline (413.8 g, 1 eq.) was dissolved in dichloromethane (1.65 L). The solution was heated to reflux and then filtered through a layer of Celite(® filter agent. The filtrate was cooled to 5° C. with stirring. Triethylamine (305.4 mL, 1.1 eq.) was added in a single portion. The reaction mixture was stirred for 15 minutes. (R)-(−)-2-Amino-1-butanol (205 mL, 1.1 eq.) was added dropwise while maintaining the temperature of the reaction mixture below 40° C. The reaction mixture was allowed to stir at ambient temperature for several days. The reaction mixture was cooled to −30° C. A yellow precipitate was isolated by filtration, washed with very cold dichloromethane and then sucked dry. The solid was slurried for 1 hour with cold 80/20 water/methanol (1 L), isolated by filtration, washed with cool water, washed with very cold methanol (2×300 mL), and then sucked dry on the filter overnight to provide 475 g of (2R)-2-[(3-nitroquinolin-4-yl)amino]butan-1-ol.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. filtrationfiltered through a layer of Celite(®
  4. filtrationfilter agent
  5. stirringThe reaction mixture was stirred for 15 minutes
  6. temperaturewhile maintaining the temperature of the reaction mixture below 40° C
  7. stirringto stir at ambient temperature for several days
  8. temperatureThe reaction mixture was cooled to −30° C
  9. customA yellow precipitate was isolated by filtration
  10. washwashed with very cold dichloromethane
  11. customsucked dry
  12. customisolated by filtration
  13. washwashed with cool water
  14. washwashed with very cold methanol (2×300 mL)
  15. customsucked dry on the filter overnight

Sources & evidence

ORD record
ord-35fdaff5128e427fb31cf7cb72890d5a
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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