HCID 53650600, compound → HCID 15057056, compound

HRID 1032691Notes

Reaction equation

HRID 1032691 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O>C(O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[NH2:17]

Participants

3

Reactant 1

HCID 53650600HCID 53650600, compound

Product 1

HCID 15057056HCID 15057056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-nitro-3-pyridinyloxy)benzoic acid methyl ester, N-oxide (30 g) in 1.5 L ethanol containing 1.5 g platinum oxide was hydrogenated for five hours at 50 psi. The mixture was filtered and concentrated to 26 g solid which was purified by flash chromatography (silica, 5% methanol in dichloromethane) to give 20 g of 2-(4-amino-3-pyridinyloxy)benzoic acid methyl ester and 4.5 g solid, d 200°. The latter material was purified by flash chromatography (silica, 10% methanol in dichloromethane) to give 3.4 g solid, d 200°. This material was recrystallized from ethanol/ether to give 2.5 g solid, d 200°.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to 26 g solid which
  3. customwas purified by flash chromatography (silica, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9010445b1a974b6f935e18c785ebc56f
Source dataset
uspto-grants-1990_09
Patent number
US04959377

Reaction notes

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