Ammonium Hydroxide → 4-(2,4-dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine

HRID 1831508Notes

Reaction equation

HRID 1831508 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:10]=1[N+:21]([O-])=O.[NH4+].[OH-].[O-]S(S([O-])=O)=O.[Na+].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:10]=1[NH2:21]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 22052080[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine

Product 1

HCID 627056514-(2,4-dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamineYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine (0.20 g, 0.56 mmol was dissolved in dioxane (8 mL) and H2O (8 mL), followed by conc. NH4OH (0.3 mL) and Na2S2O4 (0.79 g, 4.53 mmol) and stirred at room temperature for 4 h. The solution was extracted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to produce 0.13 g (72%) of 4-(2,4-dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine: MS (AP) m/z 326.2 [(M+H)+, 90].

Workup

  1. extractionThe solution was extracted with EtOAc
  2. washwashed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46c5ad2a8bd344ce8d00ec33eb36746c
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

Loading…