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

HRID 1831503Notes

Reaction equation

[CH:1]1([CH:4]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[CH:1]1([CH:4]([NH:8][C:9]2[C:14]([NH2:15])=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052181(1-Cyclopropyl-butyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine

Product 1

HCID 62705650N2-(1-cyclopropyl-butyl)-4-(2,4-dichloro-phenyl)-pyridine-2,3-diamineYield 72.2%

Procedure

(1-Cyclopropyl-butyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine (0.66 g, 1.74 mmol) and Na2S2O4 (2.45 g, 14.0 mmol) were treated substantially as described in Part E of Example 9 to yield 0.44 g (72%) of N2-(1-cyclopropyl-butyl)-4-(2,4-dichloro-phenyl)-pyridine-2,3-diamine: MS (AP) m/z 350.3 [(M+H)+, 100].

Sources & evidence

ORD record: ord-339f2afd817d4a2d9e59cb0f7ecca817
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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