Hydrazine hydrate (1:1) → HCID 59442006, compound

HRID 1014222Notes

Reaction equation

HRID 1014222 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=1.O.NN>CO>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:17][CH3:18])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59441758HCID 59441758, compound

Product 1

HCID 59442006HCID 59442006, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S)-3-methyl-4-[3-(methyloxy)-4-nitrophenyl]morpholine (2.46 g, 9.76 mmol), FeCl3 (0.400 g, 2.44 mmol), activated carbon (2.0 g), and hydrazine hydrate (2.5 mL, 78 mmol) was heated in methanol (150 mL) for 3 hours. Once the starting material was judged consumed by thin layer chromatography (10% MeOH/CH2CL2) the mixture was filtered over celite and concentrated to give 4-[(3S)-3-methyl-4-morpholinyl]-2-(methyloxy)aniline as a dark purple solid (1.76 g, 7.93 mmol, 81% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.90 (d, J=6.60 Hz, 3 H), 2.95 (dd, J=6.97, 3.30 Hz, 1 H), 2.98-3.06 (m, 1 H), 3.28 (td, J=6.42, 3.30 Hz, 1 H), 3.50 (dd, J=11.00, 6.60 Hz, 1 H), 3.64 (d, J=13.20 Hz, 2 H), 3.76-3.82 (m, 1 H), 3.83 (s, 3 H), 3.84-3.90 (m, 2 H), 6.50 (dd, J=8.43, 2.20 Hz, 1 H), 6.56 (s, 1 H), 6.66 (d, J=8.43 Hz, 1 H).

Workup

  1. customOnce the starting material was judged consumed by thin layer chromatography (10% MeOH/CH2CL2) the mixture
  2. filtrationwas filtered over celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d46272ec6d4147d387ea872602319db9
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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