Sodium Dithionite → 4-(2,4-dichloro-phenyl)-N2-(1-methyl-butyl)-pyridine-2,3-diamine

HRID 1831494Notes

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][CH2:18][CH3:19])[C:10]=1[N+:21]([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[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][CH2:18][CH3:19])[C:10]=1[NH2:21]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052043[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methyl-butyl)-amine

Product 1

HCID 627056474-(2,4-dichloro-phenyl)-N2-(1-methyl-butyl)-pyridine-2,3-diamineYield 96%

Procedure

[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methyl-butyl)-amine (0.25 g, 0.71 mmol) and Na2S2O4 (1.00 g, 5.72 mmol) were treated substantially as described in Part E of Example 9 to yield 0.22 g (96%) of crude 4-(2,4-dichloro-phenyl)-N2-(1-methyl-butyl)-pyridine-2,3-diamine: MS (AP) m/z 324.3 [(M+H)+, 76].

Sources & evidence

ORD record: ord-fcb90fcad266408a8d402ac8fadd87cb
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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