7-Nitro-1,2,3,4-tetrahydroquinoline → 1,2,3,4-Tetrahydroquinolin-7-amine

HRID 2294483Notes

Reaction equation

HRID 2294483 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 152196191,2,3,4-Tetrahydroquinolin-7-amineYield 101.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-nitro-1,2,3,4-tetrahydroquinoline (396 mg, 0.0022 mol) in 4 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with PdC 10% (40 mg) at rt for 2 h. Filtration over celite afforded 330 mg (100%) of 7-amino-1,2,3,4-tetrahydroquinoline. Data for 7-amino-1,2,3,4-tetrahydroquinoline: 1H NMR (400 MHz, CDCl3) 6.72 (d, J=7.9, 1H), 6.00 (dd, J=7.9, 2.3, 1H), 5.84 (d, J=2.3, 1H), 3.67 (bs, 1H), 3.42 (bs, 2H), 3.24 (t, J=5.0, 2H), 2.65 (t, J=6.4, 2H), 1.91 (quintet, J=6.0 Hz. 2H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-e94770102a5047bfb7792f20cd9b1dc8
Source dataset
uspto-grants-1997_11
Patent number
US05688810

Reaction notes

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