3,3-Dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester → 2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

HRID 2045151Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[C:10]([CH3:26])([CH3:25])[CH2:9]2)=[O:5])[CH3:2]>C(O)C.Cl.[Fe]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[C:10]([CH3:25])([CH3:26])[CH2:9]2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (10 g, 28 mmol) in ethanol 95% (150 mL) and 10% hydrochloric acid (20 mL) was added iron (4.74 g, 85 mmol). The reaction mixture was stirred at 95° C. for 4 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo. 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 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (8.7 g, 95%) as a light yellow solid: LC/MS m/e calcd for C20H24N2O2 (M+H)+: 325.43, observed: 325.2.

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-c6e69d958b3e4175bedfb8bb5aeaec45
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586747B2

Reaction notes

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