Sodium borohydride → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

HRID 2167631Notes

Reaction equation

HRID 2167631 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:13][CH:12]=[CH:11][CH:10]=2)([O-])=O>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:3][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 22381766tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamate

Product 1

HCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamateYield 85.7%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Nickel(II) chloride hexahydrate (18.4 g) was dissolved in MeOH (360 mL) and cooled to 5° C. Sodium borohydride (2.9 g) was added followed by the product from step (i) (28 g). More sodium borohydride (11.7 g) was added slowly keeping the temperature below 23° C. then stirred for 1 h. The reaction mixture was filtered through celite and the filtrate was poured into sodium bicarbonate solution (300 mL). The solvent was reduced by half and then extracted with chloroform, combined organics were dried, and solvent removed to give the subtitle compound as a solid (22 g); MS multimode (+) 331

Workup

  1. customthe temperature below 23° C.
  2. filtrationThe reaction mixture was filtered through celite
  3. additionthe filtrate was poured into sodium bicarbonate solution (300 mL)
  4. extractionextracted with chloroform
  5. customcombined organics were dried
  6. customsolvent removed

Sources & evidence

ORD record
ord-c236b185a34b495498003e938f7129be
Source dataset
uspto-grants-2015_06
Patent number
US09045472B2

Reaction notes

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