Hydrazine hydrate (1:1) → HCID 53392453, compound

HRID 1922486Notes

Reaction equation

HRID 1922486 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1.O.NN>CO.[Ni]>[CH3:19][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([NH2:16])=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53392264HCID 53392264, compound

Product 1

HCID 53392453HCID 53392453, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N,N-dimethyl-3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propan-1-amine (600 mg, 2.278 mmol) in methanol (12 ml) was added Raney nickel (60 mg, 2.278 mmol) followed by hydrazine hydrate (1.108 ml, 22.78 mmol). The resulting mixture was then stirred at 60° C. and monitored by TLC for consumption of the starting material. The reaction mixture was then filtered through celite and the filtrate was concentrated. The residue was then dissolved in dichloromethane, dried, filtered and concentrated to give a dark oil. 1H NMR (DMSO-d6) δ 6.37-6.34 (m, 1H), 6.30-6.26 (m, 1H), 6.22-6.20 (m, 1H), 4.17 (brs, 2H), 3.12-3.03 (m, 4H), 2.55 (t, J=6.45 Hz, 2H), 2.20 (t, J=6.9 Hz, 2H), 2.11 (s, 6H), 1.79 (quint, J=6 Hz, 2H), 1.56 (quint, J=7.12 Hz, 2H). ESI-MS (m/z, %) 234 (MH+, 100), 161 (60).

Workup

  1. custommonitored by TLC for consumption of the starting material
  2. filtrationThe reaction mixture was then filtered through celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was then dissolved in dichloromethane
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a dark oil

Sources & evidence

ORD record
ord-5040a45477834e22b043047e6e38fdd0
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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