HCID 10049710, compound → HCID 9979889, compound

HRID 1609721Notes

Reaction equation

HRID 1609721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:27]([O-])=O)[CH:5]=[C:6]([Cl:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[C:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=1>[Pt].C(O)C>[Cl:26][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18])=[C:11]([CH:23]([CH3:24])[CH3:25])[CH:10]=1)[NH2:27]

Participants

4

Reactant 1

HCID 10049710HCID 10049710, compound

Product 1

HCID 9979889HCID 9979889, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dichloro-4-(3'-isopropyl-4'-t-butyldimethylsiloxyphenoxy)-nitrobenzene and 1.15 g of 10% platinum on carbon in 200 ml of ethanol is hydrogenated on a Parr shaker. Catalyst is removed by tinting through Celite and the filtrate stripped to afford 3,5-dichloro4-(3'-isopropyl-4'-t-butyldimethylsiloxyphenoxy)-aniline. This is dissolved with 3.08 ml of ethyl bromoacetate and 3.43 g of diisopropylethylamine in 50 ml dimethylformamide and heated at 140° for 18 hours. Solvent is removed with high vacuum and the residue taken up 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 85:15 to 80:20 hexane:ethyl acetate as eluent affords ethyl N-[3,5-dichloro-4-(3'-isopropyl-4'-t-butyldimethylsiloxyphenoxy)phenyl]aminoacetate. NMR (CDCl3): δ0.2 (6H,s), 1.0 (9H,s), 1.2 (6H,d), 1.3 (3H,t), 3.3 (1H,m), 3.9 (2H,d), 4.3 (2H,q), 4.4 (1H,t), 6.4 (1H,d of d), 6.6 (2H,s), 6.6 (1H,d), 6.9 (1H,d).

Workup

  1. customCatalyst is removed

Sources & evidence

ORD record
ord-dfbfce66b86d4870aa9610f5caf8ac18
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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