HCID 10477306, compound → HCID 19030106, compound

HRID 2256494Notes

Reaction equation

HRID 2256494 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 fitration through Celite and the fitrate 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): δ 1.3 (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 fitration through Celite

Sources & evidence

ORD record
ord-07e189b2bdbb4389b564277ed6a76464
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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