HCID 10477306, compound → HCID 19030106, compound

HRID 866013Notes

Reaction equation

HRID 866013 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:26]([O-])=O)[CH:5]=[C:6]([Cl:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:10]=1>[Pt].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:10]=1)[NH2:26]

Participants

4

Reactant 1

HCID 10477306HCID 10477306, compound

Product 1

HCID 19030106HCID 19030106, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dichloro-4-[3'-(4-fluorobenzyl)-4'-methoxyphenoxy]nitrobenzene (3.64 g) and 360 mg of 10% platinum on carbon in 200 ml ethanol is hydrogenated on a Parr shaker. Catalyst is removed by filtration through Celite and the filtrate stripped to afford 3,5-dichloro-4-[3'-(4-fluorobenzyl)-4'-methoxyphenoxy]-aniline. This is redissolved with 1.10 ml ethyl bromoacetate and 1.28 g of diisopropylethylamine in 30 ml dimethylformamide and heated at 140° for 18 hours. Solvent is removed with high vacuum and the residue dissolved in ethyl acetate and extracted twice with water. The ethyl acetate is dried, filtered and stripped to give crude product Chromatography on silica gel with 80:20 to 70:30 hexane:ethyl acetate affords pure ethyl N-[3,5-dichloro-4-[3'-(4-fluorobenzyl)-4'-methoxyphenoxy]-phenyl]aminoacetate; NMR (CDCl3): δ1.3 (3H, t), 3.7 (3H, s), 3.9 (2H, s), 3.9 (2H, s), 4.3 (2H, q), 6.6 (1H, d of d), 6.7 (1H, d), 6.8 (1H, d), 6.9 (2H, m), 7.1 (2H, m), 7.3 (2H, s).

Workup

  1. customCatalyst is removed by filtration through Celite

Sources & evidence

ORD record
ord-f6c3b0dc88024c76a87a84d8c3706a0d
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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