2,2-Diethyl-1,2,3,4-tetrahydro-7-nitroquinoline → 7-Amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline

HRID 1861743Notes

Reaction equation

HRID 1861743 reaction equation
NC1C=C2C(CCC(C)(C)N2)=CC=1.[CH2:14]([C:16]1([CH2:29][CH3:30])[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][C:20]([N+:26]([O-])=O)=[CH:21][CH:22]=2)[NH:17]1)[CH3:15]>CCOC(C)=O.CCO.[Pd]>[NH2:26][C:20]1[CH:19]=[C:18]2[C:23]([CH2:24][CH2:25][C:16]([CH2:29][CH3:30])([CH2:14][CH3:15])[NH:17]2)=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 105138652,2-Diethyl-1,2,3,4-tetrahydro-7-nitroquinolineHCID 105352872,2-Dimethyl-1,2,3,4-tetrahydroquinolin-7-amine

Product 1

HCID 107268997-Amino-2,2-diethyl-1,2,3,4-tetrahydroquinolineYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared in a manner similar to that described for 7-amino-1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 19 of Scheme III, where R1=R2=Me) from for 2,2-diethyl-1,2,3,4-tetrahydro-7-nitroquinoline (0.311 g, 1.33 mmol) and 10% Pd/C (31 mg, 10% by weight) in EtOAc (4.0 mL) and EtOH (4.0 mL) to afford 255 mg (94%) of 7-amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline. Data for 7-amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.26 (4:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.77 (d, J=7.9H, 1H), 6.12 (dd, J=7.9,1.9,1H), 6.05 (d,J=2.0,1H), 4.68 (broad s,3H), 2.62 (t, J=6.7, 2H), 1.67 (t, J=6.7, 2H), 1.38-1.55 (m, 4H), 0.85 (t, J=7.4, 6H). P 2,2-Diethyl-7-fluoro-1,2,3,4-tetrahydro-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (Compound 120, Structure 20 of Scheme III, where R1, R2=Et, R3=trifluoromethyl, R4=F)

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-9ce4b3f5d0f44770be5b8212d39ce3fa
Source dataset
uspto-grants-2003_03
Patent number
US06534516B1

Reaction notes

Loading…