Sodium borohydride → N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydroquinolin-2,3,4-triamine

HRID 1757100Notes

Reaction equation

HRID 1757100 reaction equation
[BH4-].[Na+].[C:3]1([CH2:9][N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:11]2[C:20]([N+:21]([O-])=O)=[C:19]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.C(Cl)Cl.O.[Ni](Cl)Cl>[C:33]1([CH2:32][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11]2[C:20]([NH2:21])=[C:19]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 57070605N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydro-3-nitroquinolin-2,4-diamine

Product 1

HCID 57018445N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydroquinolin-2,3,4-triamineYield 92.9%

Reagents, catalysts & solvents 3

HCID 16212333Nickel chloride hydrateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (0.82 g, 22 mmole) was added to a solution of nickel(II) chloride hydrate (1.43 g, 6 mmole) in methanol (300 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for about 30 minutes. A solution containing N2,N2,N4 -Tris(phenylmethyl)-5,6,7,8-tetrahydro-3-nitroquinolin-2,4-diamine (5.73 g, 12 mmole) in methylene chloride (20 mL) was added followed by 5 successive additions of sodium borohydride (0.38 g, 10 mmole each addition). The reaction mixture was stirred at ambient temperature for about 15 minutes then filtered through a layer of silica gel. The filtrate was evaporated. The residue was taken up in a minimum amount of methylene chloride then placed on a layer of silica gel. The silica gel was eluted with hexane:ethyl acetate 80:20. The organic phase was collected then evaporated to provide 5.0 g of the desired product as a green oil.

Workup

  1. additionThe addition
  2. customto form along with gas evolution
  3. additionwas added
  4. stirringThe reaction mixture was stirred at ambient temperature for about 15 minutes
  5. filtrationthen filtered through a layer of silica gel
  6. customThe filtrate was evaporated
  7. washThe silica gel was eluted with hexane:ethyl acetate 80:20
  8. customThe organic phase was collected
  9. customthen evaporated

Sources & evidence

ORD record
ord-ca15d9f5fa4b48afb06215ae3e0eee1e
Source dataset
uspto-grants-1995_08
Patent number
US05444065

Reaction notes

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