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

HRID 1831564Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH:22]2[CH2:24][CH2:23]2)[CH2:20][CH3:21])[C:13]=1[N+:25]([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH:22]2[CH2:24][CH2:23]2)[CH2:20][CH3:21])[C:13]=1[NH2:25]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052129[4-(2-Chloro-4-trifluoromethyl-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine

Product 1

HCID 696580544-(2-chloro-4-trifluoromethyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamineYield 94%

Procedure

[4-(2-Chloro-4-trifluoromethyl-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine (0.55 g, 1.38 mmol) and Na2S2O4 (1.93 g, 11.1 mmol) were treated substantially as in Part E of Example 9 to yield 94% of 4-(2-chloro-4-trifluoromethyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine: MS (AP) m/z 369.8 [(M+H)+, 100].

Sources & evidence

ORD record: ord-06e92bbff0eb4f4cbd1c3bc0ad849cc3
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

Loading…