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

HRID 1831529Notes

Reaction equation

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

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052173[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine

Product 1

HCID 696581484-(2-chloro-4-methoxy-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamineYield 241.7%

Procedure

[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine (0.10 g, 0.27 mmol) and Na2S2O4 (0.38 g, 2.21 mmol) were treated substantially as described in Part E of Example 9 to give 0.21 g (81%) 4-(2-chloro-4-methoxy-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine: MS (AP) m/z 321.8 [(M+H)+, 100].

Sources & evidence

ORD record: ord-5567b97377bc4cbb80e6497434753ac8
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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