Ammonium Hydroxide → 5-Nitropyridine-2,4-diamine

HRID 854079Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2N=C(C3C=CC([N+]([O-])=O)=CC=3)[NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].[NH4+:22].[OH-]>>[NH2:10][C:7]1[CH:6]=[C:5]([NH2:22])[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 178526539HCID 178526539, compound

Product 1

HCID 218138965-Nitropyridine-2,4-diamineYield 77%

Procedure

A solution of 4-amino-2-chloro-5-nitropyridine (4) (1.0 g, 5.76 mmol) in 50 ml 28% NH4OH was heated in a sealed tube at 120° C. for overnight. After cooling the reaction mixture to room temperature afforded orange red solid 5 (0.770 g, 77%). 1H NMR (DMSO-d6, 500 MHz): δ 8.66 (1H, s), 7.35 (1H, br s), 6.73 (1H, brs), 5.67 (1H, s); EIMS m/z: 155.2 (M+1), 153.2 (M−1)

Sources & evidence

ORD record: ord-9179830a868748bcb7d312b29a456325
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256287B2

Reaction notes

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