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

HRID 540807Notes

Reaction equation

HRID 540807 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 a brown semi-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-0e296ca965bb47b98f86f75d6e422b3e
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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