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

HRID 1831525Notes

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]([CH:20]2[CH2:23][CH2:22][CH2:21]2)[CH2:18][CH3:19])[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]([CH:20]2[CH2:21][CH2:22][CH2:23]2)[CH2:18][CH3:19])[C:11]=1[NH2:24]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 22052220[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-propyl)-amine

Product 1

HCID 696581654-(2-chloro-4-methoxy-phenyl)-N2-(1-cyclobutyl-propyl)-pyridine-2,3-diamineYield 151.1%

Procedure

[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-propyl)-amine (0.33 g, 0.88 mmol) and Na2S2O4 (1.33 g, 7.6 mmol) were treated substantially as described in Part E of Example 9 to give 0.46 g (100%) 4-(2-chloro-4-methoxy-phenyl)-N2-(1-cyclobutyl-propyl)-pyridine-2,3-diamine: MS (AP) m/z 345.9 [(M+H)+, 100].

Sources & evidence

ORD record: ord-8b8a71b1015846779c10368c9b45a358
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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