Hydrazine → HCID 57917192, compound

HRID 2093623Notes

Reaction equation

HRID 2093623 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:13].NN>CO.O.O.O.O.O.O.[Fe](Cl)Cl>[NH2:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:13])[C:2]=1[OH:1])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 67141374HCID 67141374, compound

Product 1

HCID 57917192HCID 57917192, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 129819097HCID 129819097, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Iron chloride hexahydrate (9.6 mg), 4-hydroxy-3-methyl-5-nitrobenzonitrile (126 mg), and 77 mg of activated carbon were suspended in 5 ml of methanol and heated under N2 at 70° C. for 10 min. Hydrazine (0.11 ml) was then added slowly and the mixture was stirred for 2 h at 70° C. The mixture was then cooled to room temperature and filtered through a plug of Celite, eluting with methanol. The eluent was concentrated in vacuo and the residue was purified on a 2×1500 micron preparative TLC plate, eluting with ethyl acetate (Rf=0.24), to provide 101 mg (96%) of the title compound. Mass spectrum (ESI) 150.1 (M+1). 1H NMR (500 MHz, CDCl3): □ 6.93 (s, 1H), 6.91 (s, 1H), 5.21 (bs, 1H), 3.76 (bs, 2H), 2.42 (s, 3H).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through a plug of Celite
  3. washeluting with methanol
  4. concentrationThe eluent was concentrated in vacuo
  5. customthe residue was purified on a 2×1500 micron preparative TLC plate
  6. washeluting with ethyl acetate (Rf=0.24)

Sources & evidence

ORD record
ord-3091d5a3db804dd2b8ed91cb4dc4cd0a
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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