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

HRID 265716
Notes
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Reaction equation

HRID 265716 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 hydrateCatalyst
HCID 887
Methanol
Solvent
HCID 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-981a18aba74a48cfa96e06cc43bc003a
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05648516

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes