Triethylamine → HCID 86633732, compound

HRID 415484Notes

Reaction equation

HRID 415484 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>CN(C=O)C>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 86633732HCID 86633732, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (31 g, 0.31 mol) was added to a solution of 2,4-dichloro-3-nitroquinoline (50 g of 90% pure material) in anhydrous DMF (400 mL). 4-Amino-1-butanol (21 mL, 0.23 mol) was added in portions over a period of ten minutes, and the reaction was stirred at room temperature overnight and then partitioned between deionized water (1.5 L) and ethyl acetate (800 mL). The organic layer was separated, and a precipitate formed. The precipitate was collected by filtration, and the filtrate was concentrated under reduced pressure to provide a solid. The two solids were dried under vacuum to provide 44.34 g of 4-(2-chloro-3-nitroquinolin-4-ylamino)butan-1-ol.

Workup

  1. custompartitioned between deionized water (1.5 L) and ethyl acetate (800 mL)
  2. customThe organic layer was separated
  3. customa precipitate formed
  4. filtrationThe precipitate was collected by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto provide a solid
  7. customThe two solids were dried under vacuum

Sources & evidence

ORD record
ord-0613c3d00681486abfb2dcea22a20bef
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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