Hydrazine hydrate (1:1) → (3-Methoxy-4-nitrophenyl)hydrazine

HRID 59281Notes

Reaction equation

HRID 59281 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.O.[NH2:14][NH2:15]>C(O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:14][NH2:15])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 21883922(3-Methoxy-4-nitrophenyl)hydrazineYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (2.5 g, 14.60 mmol) in ethanol (25 mL) was added hydrazine hydrate (2.1 g, 43.8 mmol). The reaction mixture was refluxed for 3-4 h. The reaction mixture was concentrated to afford 2.0 g of desired product. 1H NMR (300 MHz, DMSO do): δ 3.84 (s, 3H), 4.46 (s, 2H), 6.31 (d, J=9.3 Hz, 1H), 6.50 (s, 1H), 7.83 (d, J=9.3 Hz, 1H), 8.25 (s, 1H); MS (m/z): (184.01 M)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3-4 h
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c406311f3875496393f8608d8aea2137
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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