Tetra-n-butylammonium 1-(3-nitrophenyl)ethanesulphonate → Tetra-n-butylammonium 1-(3-aminophenyl)ethanesulphonate

HRID 259919Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([S:12]([O-:15])(=[O:14])=[O:13])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH2:16]([N+:20]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]([S:12]([O-:15])(=[O:13])=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH2:29]([N+:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31][CH3:32]

Participants

Conditions

Temperature: 25 °C

Procedure

0.2 g of 5% strength palladium on charcoal is added to a solution of 2.8 g of the laevorotatory isomer of tetra-n-butylammonium 1-(3-nitrophenyl)ethanesulphonate in 50 cm3 of ethanol. The suspension is stirred for 2 hours at a temperature of about 25° C. under a hydrogen atmosphere (100 kPa). The catalyst is filtered off and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 2.8 g of the laevorotatory isomer of tetra-n-butylammonium 1-(3-aminophenyl)ethanesulphonate are thus obtained in the form of an oil, used as such in the subsequent syntheses.

Workup

filtrationThe catalyst is filtered off
concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record: ord-e4772676ca694072bc9fb6329cecc7d7
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523469

Reaction notes

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