HCID 21912946, compound → N4-[2-(benzyloxy)ethyl]-6-methyl-2-phenoxypyridine-3,4-diamine

HRID 1008045Notes

Reaction equation

HRID 1008045 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]=1[N+:26]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13]=1[NH2:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 21912946HCID 21912946, compound

Product 1

HCID 69875562N4-[2-(benzyloxy)ethyl]-6-methyl-2-phenoxypyridine-3,4-diamineYield 108.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen purge, 5% platinum on carbon (1.0 g) and toluene (20 mL) were added to a Parr vessel. [2-(Benzyloxy)ethyl](6-methyl-3-nitro-2-phenoxy-pyridin-4-yl)amine (4.91 g, 12.9 mmol) and additional toluene (40 mL) were then added. The vessel was placed under hydrogen pressure (49 psi, 3.3×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to yield 4.9 g of N4-[2-(benzyloxy)ethyl]-6-methyl-2-phenoxypyridine-3,4-diamine as a milky oil, contaminated with a small amount of toluene.

Workup

  1. customUnder a nitrogen purge
  2. addition5% platinum on carbon (1.0 g) and toluene (20 mL) were added to a Parr vessel
  3. customfor three hours
  4. filtrationThe reaction mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af523c9fb3ac472b8874cfe8396b888b
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

Loading…