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

HRID 1831498Notes

Reaction equation

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

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 11057630(1-Cyclopropyl-propyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine

Product 1

HCID 11110461N2-(1-cyclopropyl-propyl)-4-(2,4-dichloro-phenyl)-pyridine-2,3-diamineYield 66%

Procedure

(1-Cyclopropyl-propyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine (0.46 g, 1.26 mmol) and Na2S2O4 (1.76 g, 10.1 mmol) were treated substantially as described in Part E of Example 9 to yield 0.16 g (66%) of crude N2-(1-cyclopropyl-propyl)-4-(2,4-dichloro-phenyl)-pyridine-2,3-diamine: MS (AP) m/z 336.3 [(M+H)+, 100].

Sources & evidence

ORD record: ord-c8cd6b0dba7d4623a7c9c3b658ccb371
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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