Potassium Hydroxide → 6-Nitro-2,5-pyridinediamine

Reaction equation

C(OC([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(OCC)=O)=[C:9]([N+:19]([O-:21])=[O:20])[N:8]=1)=O)C.[OH-].[K+]>>[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([N+:19]([O-:21])=[O:20])[N:8]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 14366181HCID 14366181, compound

Product 1

HCID 98152436-Nitro-2,5-pyridinediamine

Procedure

4.0 g of the biscarbamate of Example 9 are boiled in 200 ml of an ethanolic 3 percent potassium hydroxide solution for 18 hours with reflux. This is followed by filtering and the filtrate is acidified with concentrated sulphuric acid, whereupon it is concentrated in vacuo. The residue is taken up in methanol. The desired product then crystallizes as hydrochloride (melting point 241° C.).

Workup

temperaturewith reflux
filtrationby filtering
concentrationis concentrated in vacuo
customThe desired product then crystallizes as hydrochloride (melting point 241° C.)

Sources & evidence

ORD record: ord-4764633e04894bfd9aa008fa8af608f2
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04950302

Reaction notes

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