Hydrochloric Acid → 6-Phenylpyridine-2,3-diamine

HRID 1437464Notes

Reaction equation

[N+:1]([C:4]1[C:5]([NH2:16])=[N:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-])=O.Cl.[OH-].[Na+]>[Fe].CO>[C:10]1([C:7]2[N:6]=[C:5]([NH2:16])[C:4]([NH2:1])=[CH:9][CH:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 3-nitro-6-phenyl-2-pyridine amine (Compound of Reference Example 112) (0.8 g), iron filings (1.3 g) and methanol (7 ml) was cooled with ice and to the suspension was added dropwise concentrated hydrochloric acid (3 ml). After the dropwise addition, the mixture was stirred at room temperature for 10 minutes and at 80° C. for 50 minutes. The reaction mixture was poured onto ice, neutralized with an aqueous solution of 8 N sodium hydroxide and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v) (At that time, insolubles were filtered off by means of celite). The organic layer was dried over MgSO4, and the solvent was distilled off under reduced pressure. The resulting crystals were collected by filtration to obtain 6-phenyl-2,3-pyridine diamine (0.7 g, 99%).

Workup

temperaturewas cooled with ice and to the suspension
additionAfter the dropwise addition
additionThe reaction mixture was poured onto ice
extractionextracted with ethyl acetate-tetrahydrofuran (3:1
filtrationv/v) (At that time, insolubles were filtered off by means of celite)
dry with materialThe organic layer was dried over MgSO4
distillationthe solvent was distilled off under reduced pressure
filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record: ord-97c6624e89b743e09a30345fe3d1c220
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622479B2

Reaction notes

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