Hydrazine → HCID 59441910, compound

HRID 1014188Notes

Reaction equation

HRID 1014188 reaction equation
NN.[CH3:3][CH:4]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH3:22])[CH:13]=2)[CH2:8][CH2:7]1)[CH3:5]>>[CH3:5][CH:4]([N:6]1[CH2:7][CH:8]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:21][CH3:22])[CH:13]=2)[CH2:10][CH2:11]1)[CH3:3]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 59442056HCID 59442056, compound

Product 1

HCID 59441910HCID 59441910, compoundYield 90.6%

Procedure

In a manner analgous to the hydrazine-mediated reduction of Intermediate B1, 4-[1-(1-methylethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-2-(methyloxy)aniline (1.60 g, 90% yield) was prepared from 1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (2.0 g, 7.17 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.12 (d, J=6.6 Hz, 6 H), 2.54 (s, 2 H), 2.73 (t, J=5.5 Hz, 2 H), 2.79 (dt, J=12.9, 6.6 Hz, 1 H), 3.24 (d, J=3.3 Hz, 2 H), 3.77 (s, 2 H), 3.85 (s, 3 H), 5.94 (s, 1 H), 6.65 (d, J=8.1 Hz, 1H), 6.80-6.86 (m, 2 H).

Sources & evidence

ORD record
ord-d0435978ca4b4a1b85553f13d487a0b9
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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