Ammonium Hydroxide → HCID 86591986, compound

HRID 1831534Notes

Reaction equation

HRID 1831534 reaction equation
[CH:1]1([CH:4]([NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[CH3:25])[CH:11]=[CH:10][N:9]=2)[CH2:5][CH3:6])[CH2:3][CH2:2]1.[NH4+].[OH-].[O-]S(S([O-])=O)=O.[Na+].[Na+]>O1CCOCC1.O>[CH:1]1([CH:4]([NH:7][C:8]2[C:13]([NH2:14])=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[CH3:25])[CH:11]=[CH:10][N:9]=2)[CH2:5][CH3:6])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 22052063(1-Cyclopropyl-propyl)-[4-(4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine

Product 1

HCID 86591986HCID 86591986, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(1-Cyclopropyl-propyl)-[4-(4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine (0.220, 0.64 mmol) was dissolved in dioxane (10 mL) and H2O (10 mL), followed by conc. NH4OH (0.4 mL) and Na2S2O4 (0.906 g, 5.2 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 the crude intermediate N2-(1-cyclopropyl-propyl)-4-(4-methoxy-2-methyl-phenyl)-pyridine-2,3-diamine; MS(AP) m/z 312.2 [(M+H)+, 100]. The crude intermediate was used in the following step.

Workup

  1. extractionThe solution was extracted with EtOAc
  2. washwashed with H2O, brine, dried Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ee7a59acdd84483b697e471cc152b2c
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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