HCID 10316208, compound → Benzenamine, 3,5-dichloro-4-[4-methoxy-3-(1-methylethyl)phenoxy]-

HRID 2256482Notes

Reaction equation

HRID 2256482 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1>[Pt].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:18])[CH3:19])[CH:10]=1)[NH2:21]

Participants

4

Reactant 1

HCID 10316208HCID 10316208, compound

Product 1

HCID 10245806Benzenamine, 3,5-dichloro-4-[4-methoxy-3-(1-methylethyl)phenoxy]-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dicloro-4-(3'-isopropyl-4'-methoxyphenoxy)-nitrobenzene (2.0 g) and 200 mg. of 10% platinum on carbon in 100 ml. of ethanol are hydrogenated on a Parr shaker. Catalyst is then removed by filtration through Celite and the filtrate is stripped to afford 3,5-dicloro-4-(3'-isopropyl-4'-methoxyphenoxy)-aniline. To this is added 30 g of dimethyl oxalate and this is stirred at 120° for 4 hours. Excess oxalate is removed under high vacuum from a hot water bath and the residue is chromatographed on silica gel with 9:1 toluene:ethyl acetate affording methyl N-[3,5-dichloro-4-(4'-methoxy-3'-isopropylphenoxy)-phenyl]-oxamate; NMR(CDCl3): δ 1.2 (6H,d), 3.3 (1H,m), 3.8 (3H,s), 4.0 (3H,s), 6.5 (1H,d of d), 6.7 (1H,d), 6.8 (1H,d), 7.7 (2H,s).

Workup

  1. customCatalyst is then removed by filtration through Celite

Sources & evidence

ORD record
ord-e65a9478da8f43e0a4f198b583bf4eff
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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