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

HRID 1831516Notes

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]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:11]=1[N+:24]([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]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:11]=1[NH2:24]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052147[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-propyl-butyl)-amine

Product 1

HCID 696582994-(2-chloro-4-methoxy-phenyl)-N2-(1-propyl-butyl)-pyridine-2,3-diamineYield 171.8%

Procedure

[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-propyl-butyl)-amine (0.31 g, 0.82 mmol) and Na2S2O4 (1.15 g, 6.62 mmol) were treated substantially as described in Part E of Example 9 to give 0.49 g (100%) 4-(2-chloro-4-methoxy-phenyl)-N2-(1-propyl-butyl)-pyridine-2,3-diamine: MS (AP) m/z 347.9 [(M+H)+, 100].

Sources & evidence

ORD record: ord-9f156d0a898a46048aa73422956a231a
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

Loading…