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

HRID 1831512

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]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=1[N+:22]([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]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=1[NH2:22]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052219[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

Product 1

HCID 696580374-(2,4-dichloro-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamineYield 59%

Procedure

[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine (2.11 g, 5.72 mmol) and Na2S2O4 (8.03 g, 46.1 mmol) were treated substantially as described in Part E of Example 9 to yield 1.14 g (59%) of 4-(2,4-dichloro-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine: MS (AP) m/z 340.2 [(M+H)+, 100].

Sources & evidence

ORD record: ord-02c441edc10f41118ef12a6062fc4cf4
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Linked notes

Loading…