Ammonium Hydroxide → N2-sec-butyl-4-(2-chloro-4-difluoromethoxy-phenyl)-2,3-dihydro-pyridine-2,3-diamine

HRID 1831552Notes

Reaction equation

HRID 1831552 reaction equation
[CH:1]([NH:5][CH:6]1[CH:11]([N+:12]([O-])=O)[C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][C:16]=2[Cl:25])=[CH:9][CH:8]=[N:7]1)([CH2:3][CH3:4])[CH3:2].[NH4+].[OH-].[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[CH:1]([NH:5][CH:6]1[CH:11]([NH2:12])[C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][C:16]=2[Cl:25])=[CH:9][CH:8]=[N:7]1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 22052136Sec-butyl-[4-(chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridin-2-yl]-amine

Product 1

HCID 86591992N2-sec-butyl-4-(2-chloro-4-difluoromethoxy-phenyl)-2,3-dihydro-pyridine-2,3-diamineYield 97%

Procedure

Sec-butyl-[4-(chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridin-2-yl]-amine (0.163, 0.44 followed by conc. NH4OH (0.4 mL) and Na2S2O4 (0.62 g, 3.55 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 0.145 g (97%) of N2-sec-butyl-4-(2-chloro-4-difluoromethoxy-phenyl)-2,3-dihydro-pyridine-2,3-diamine as a yellow oil.

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-5ec4050e3b344a33832458750e2835ff
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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