Ethanol → 2-Hydrazino-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine

HRID 1266925Notes

Reaction equation

HRID 1266925 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]([F:21])([F:20])[C:11]([F:19])([F:18])[C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])[N:3]=1.C(O)C.O.[NH2:26][NH2:27]>O>[NH:26]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]([F:21])([F:20])[C:11]([F:19])([F:18])[C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])[N:3]=1)[NH2:27]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 24654Hydrazine hydrate (1:1)HCID 185447902-Fluoro-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine

Product 1

HCID 185447822-Hydrazino-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridineYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, a reaction flask was loaded with 2-fluoro-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine (10 g) and ethanol (8 ml), followed by dropwise addition of a mixture of hydrazine monohydrate (7.7 g) and ethanol (8 ml) to the flask in 30 minutes with stirring. After the dropwise addition was ended, stirring was continued at 55 to 65° C. for one hour. The heating was stopped, and water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was condensed to give 2-hydrazino-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine (10 g).

Workup

  1. additionAfter the dropwise addition
  2. stirringstirring
  3. extractionfollowed by extraction with ethyl acetate
  4. customcondensed

Sources & evidence

ORD record
ord-5d562148bb5746f3b164e99fd56855db
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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