Hydrazine hydrate (1:1) → HCID 59144174, compound

HRID 424514Notes

Reaction equation

HRID 424514 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][S:9][C:8]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:7]1=2)[CH3:2].O.NN>CO.[Ni]>[CH2:19]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][S:9][C:8]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:7]1=2)[CH3:20]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59144090HCID 59144090, compound

Product 1

HCID 59144174HCID 59144174, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of N,N-diethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine (1.109 g, 3.76 mmol) in MeOH (30 mL) was added Raney-Nickel (slurry in water; ˜0.1 g, 3.76 mmol) followed by hydrazine hydrate (1.828 mL, 37.6 mmol). The mixture was immersed in a preheated oil bath and refluxed for 30 minutes. The solution was cooled to room temperature, filtered through Celite, and washed with MeOH. The crude material was filtered through a silica plug (3.5% (2M NH3 in MeOH):CH2Cl2). The solvent was evaporated to give the product as dark brown oil (1.07 g, quantitative). 1H NMR (CDCl3) δ 6.58 (d, J=8.7 Hz, 1H), 6.45 (d, J=2.7 Hz, 1H), 6.40 (dd, J=2.7, 8.7 Hz, 1H), 3.53-3.50 (m, 2H), 3.30 (m, 4H), 3.03-2.99 (m, 2H), 1.03 (t, J=7.2 Hz, 6H); ESI-MS (m/z, %): 268, 266 (MH+, 100), 100 (52).

Workup

  1. customThe mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 30 minutes
  3. filtrationfiltered through Celite
  4. washwashed with MeOH
  5. filtrationThe crude material was filtered through a silica plug (3.5% (2M NH3 in MeOH):CH2Cl2)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-39103a7c234a494f9eb414335a217ca9
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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