Sodium borohydride → 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine

HRID 2383087Notes

Reaction equation

HRID 2383087 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[C:16]([N+:21]([O-])=O)[CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.ClCCl.[Ni](Cl)Cl>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[C:16]([NH2:21])[CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 67050925(7-Benzyloxy-3-nitroquinolin-4-yl)(2-methylpropyl)amine2×

Product 1

HCID 670509707-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamineYield 89.8%

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Sodium borohydride (29.0 g, 0.767 mol) was added in small portions to a solution of nickel(II)chloride (22.8 g, 0.096 mol) in methanol (1.25 L). A solution of (7-benzyloxy-3-nitroquinolin-4-yl)-(2-methylpropyl)amine (67.4 g, 0.192 mol) in methanol (300 mL) and dichloromethane (300 mL) was added to the resulting mixture. A precipitate was present and was dissolved by the addition of dichloromethane (500 mL). Additional sodium borohydride (˜10 g) was added in small portions until the (7-benzyloxy-3-nitroquinolin-4-yl)-(2-methylpropyl)amine was consumed. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with 50:50 dichloromethane:methanol. The filtrate was concentrated under reduced pressure, and the black, oily residue was treated with water and dichloromethane. The organic solution was washed with water and brine, dried over magnesium sulfate, and filtered. The filtrate was treated with activated charcoal, filtered, and concentrated under reduced pressure to yield 55.4 g of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine as an oily brown solid.

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with 50:50 dichloromethane
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionthe black, oily residue was treated with water and dichloromethane
  7. washThe organic solution was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. additionThe filtrate was treated with activated charcoal
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef18e6fafc7c477583604398111b7778
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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