Hydrochloric Acid → 1-(Quinolin-6-yl)cyclopropan-1-amine

HRID 876793

Reaction equation

HRID 876793 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.B(F)(F)F.CCOCC.Cl.[OH-].[Na+]>CCOCC>[N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3([NH2:16])[CH2:2][CH2:1]3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 592995Quinoline-6-carbonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 630972281-(Quinolin-6-yl)cyclopropan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethylmagnesium bromide (7.7 mmol, 3 M in ethyl ether) was added to a solution of quinoline-6-carbonitrile (0-4) (540 mg, 3.5 mmol) and Ti(Oi-Pr)4 (3.9 mmol, 1.16 mL) in Et2O (15 mL) at −70° C. The resulting yellow solution was stirred for 10 mins, warmed to room temperature over 1.5 h, and then was treated with BF3.OEt2 (7 mmol, 0.88 mL). The resulting mixture was stirred for 1 h. Then 1N aqueous HCl (11 mL) and ethyl ether (40 mL) were added, followed by NaOH (10% aq, 30 mL). The mixture was extracted with ethyl ether. The combined ethyl ether layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the crude title compound, which was used for the next step without further purification. MS (m/z): 185 (M+1)+.

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. extractionThe mixture was extracted with ethyl ether
  3. dry with materialThe combined ethyl ether layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b44d7f2fca014da9aa91f74bc59e9afa
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Linked notes

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