N-Ethyl-N-(6-nitroquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine → N-ethyl-N-(6-aminoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine

HRID 1031980Notes

Reaction equation

HRID 1031980 reaction equation
[CH2:1]([N:3]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][CH:21]=1)[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:15]([O-])=O)[CH:11]=2)[N:6]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([N:3]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:22][CH:21]=1)[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:15])[CH:11]=2)[N:6]=1)[CH3:2]

Participants

4

Reactant 1

HCID 19813443N-Ethyl-N-(6-nitroquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine

Product 1

HCID 19813422N-ethyl-N-(6-aminoquinol-2-ylmethyl)-4-methanesulphonamidophenethylamineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product of part (A) (0.55 g) was catalytically hydrogenated similarly to Preparation 1(C) but using H2 over 5% Pd on C in ethyl acetate at 15 p.s.i. (103.4 kPa) for 3 hours, giving the title compound (0.51 g).

Sources & evidence

ORD record
ord-03244d1751e04231b02c148cae7ef78d
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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