N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide → N-[2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide

HRID 2045174Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1>C(O)C.Cl.[Fe]>[NH2:25][C:21]1[CH:20]=[C:19]([CH:3]2[C:2]([CH3:1])([CH3:28])[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[O:13])[CH:9]=3)[NH:4]2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (2 g, 5 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (20 mL) was added iron (0.84 g, 15 mmol). The reaction mixture was stirred at 95° C. for 1 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with 30% sodium hydroxide in water (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-[2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (1.5 g, 80%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C19H23N3O3S (M+H)+: 374.48, observed: 374.1.

Workup

filtrationThen the insoluble solid was filtered off
concentrationthe filtrate was concentrated in vacuo
extractionthe residue was extracted with ethyl acetate (2×200 mL)
washwashed with 30% sodium hydroxide in water (2×100 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-75c1150a967b4a7db59f5994190cf56c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586747B2

Reaction notes

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