Sodium Hydroxide → Hydrazine, [3-methoxy-5-(trifluoromethyl)phenyl]-

HRID 1011936Notes

Reaction equation

HRID 1011936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N:14]([O-])=O.[Na+].[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][NH2:14])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 6056715-(Trifluoromethyl)-m-anisidineHCID 23668193Sodium Nitrite

Product 1

HCID 57030420Hydrazine, [3-methoxy-5-(trifluoromethyl)phenyl]-Yield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Following the procedure described in Journal of Organic Chemistry (1972), 37(18), 2849-53, 0.5 g (2.62 mmol) of 3-methoxy-5-trifluoromethyl-phenylamine was suspended in 4.6 ml of 25% aqueous HCl, cooled (0° C.) and carefully treated (without exceeding 10° C.) with 0.189 g (2.75 mmol) of sodium nitrite dissolved in 2.7 ml of water. The solution was stirred for 1 h at this temperature and 30 min at RT. Then, 2.48 g (13.08 mmol) of tin(II) chloride in 2.5 ml of 25% aqueous HCl were dropped carefully to the cooled (0° C.) solution and stirred for 1 h. The reaction was neutralized and basified with 32% aqueous NaOH (pH14), partitioned three times between CH2Cl2 and water. The organic phase was dried over Na2SO4 and evaporated to give 0.50 g (93%) of the title compound as a yellow solid. MS: 206.8 (MH+).

Workup

  1. temperaturecooled (0° C.) solution
  2. stirringstirred for 1 h
  3. custompartitioned three times between CH2Cl2 and water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-78a9abdd4d26420daa38dae3a14bc0a9
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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