3-Nitro-N-(pyridin-4-yl)pyridin-2-amine → HCID 12445535, compound

HRID 1701702Notes

Reaction equation

HRID 1701702 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:3][CH:2]=1.[H][H]>C(O)C>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 124453923-Nitro-N-(pyridin-4-yl)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 12445535HCID 12445535, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16.5 g of 2-(4-pyridylamino)-3-nitro-pyridine in 400 ml of 95% ethanol containing 1.6 g of 10% palladized carbon was hydrogenated at 30°-40° C. at atmospheric pressure until 5.8 liters of hydrogen were absorbed and the mixture was filtered to remove the catalyst. The filtrate was evaporated to dryness and the residue was taken up in petroleum ether. The mixture was filtered to obtain 13.5 g (95% yield) of raw product melting at 202°-204° C. which was crystallized from 95% ethanol to obtain 2-(4-pyridylamino)-3-amino-pyridine in the form of a pale yellow, crystalline powder melting at 203°-205° C.

Workup

  1. customwere absorbed
  2. filtrationthe mixture was filtered
  3. customto remove the catalyst
  4. customThe filtrate was evaporated to dryness
  5. filtrationThe mixture was filtered
  6. customto obtain 13.5 g (95% yield) of raw product melting at 202°-204° C. which
  7. customwas crystallized from 95% ethanol

Sources & evidence

ORD record
ord-dc5289a80a244ddf826de2a0350af6b0
Source dataset
uspto-grants-1980_03
Patent number
US04195088

Reaction notes

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