HCID 22164899, compound → HCID 15057064, compound

HRID 1032689Notes

Reaction equation

HRID 1032689 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 22164899HCID 22164899, compound

Product 1

HCID 15057064HCID 15057064, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-[(4-nitro-3-pyridinyl)amino]phenol, N-oxide (6.2 g) in 250 ml ethanol containing 0.6 g platinum oxide was hydrogenated at 60 psi (pounds per square inch) for five hours and thereafter filtered through Celite and concentrated to 5 g oil. This was purified by flash chromatography (silica, 25% methanol in dichloromethane) to give 4.5 g solid. This was recrystallized from acetonitrile to give 3.9 g crystals, mp 174°-176°. This solid was recrystallized from acetonitrile to yield 3.2 g crystals, mp 175°-177°.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated to 5 g oil
  3. customThis was purified by flash chromatography (silica, 25% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8153e6602de148378ca4ca3ef7a17baa
Source dataset
uspto-grants-1990_09
Patent number
US04959378

Reaction notes

Loading…