Sodium Dithionite → 4-(2-chloro-4-trifluoromethyl-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine

HRID 1831567Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[C:13]=1[N+:24]([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[C:13]=1[NH2:24]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052211[4-(2-Chloro-4-trifluoromethyl-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine

Product 1

HCID 696582854-(2-chloro-4-trifluoromethyl-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamineYield 74.9%

Procedure

[4-(2-Chloro-4-trifluoromethyl-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine (0.45 g, 1.15 mmol) and Na2S2O4 (1.62 g, 9.32 mmol) were treated substantially as described in Part E of Example 9 to yield 0.31 g (74%) of 4-(2-chloro-4-trifluoromethyl-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine: MS (AP) m/z 359.8 [(M+H)+, 97].

Sources & evidence

ORD record: ord-ca93f47611b143d685d361ff65a47c9f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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