Nitric Acid → 2,2-Diethyl-1,2,3,4-tetrahydro-7-nitroquinoline

HRID 850356Notes

Reaction equation

HRID 850356 reaction equation
CC1(C)CCC2C(=CC([N+:12]([O-:14])=[O:13])=CC=2)N1.[CH2:16]([C:18]1([CH2:28][CH3:29])[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19]1)[CH3:17].[N+]([O-])(O)=O.CCOC(C)=O>S(=O)(=O)(O)O>[CH2:28]([C:18]1([CH2:16][CH3:17])[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([N+:12]([O-:14])=[O:13])=[CH:23][CH:24]=2)[NH:19]1)[CH3:29]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 105124651,2,3,4-Tetrahydro-2,2-dimethyl-7-nitroquinolineHCID 186212832,2-Diethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 105138652,2-Diethyl-1,2,3,4-tetrahydro-7-nitroquinolineYield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

This compound was prepared in a manner similar to that described for 1,2,3,4-tetrahydro-2,2-dimethyl-7-nitroquinoline (Scheme III) from for 2,2-diethyl-1,2,3,4-tetrahydroquinoline (0.955 g, 5.04 mmol) and fuming HNO3 (0.32 g, 5.0 mmol) in concentrated sulfuric acid (10 mL) to afford 0.811 g (69%) of 2,2-diethyl-1,2,3,4-tetrahydro-7-nitroquinoline after chromatography (hexanes:EtOAc, 24:1). Data for 2,2-diethyl-1,2,3,4-tetrahydro-7-nitroquinoline: Rf 0.43 (24:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 7.38 (dd, J=8.3, 2.3, 1H), 7.29 (d, J=2.3, 1H), 7.04 (d, J=8.3, 1H), 4.00 (broad s, 1H), 2.78 (t, J=6.7, 2H), 1.71 (t, J=6.7, 2H), 1.38-1.58 (m, 4H), 0.88 (t, J=7.4, 6H).

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-8adbb754284044888c94382a05614ab9
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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