Hydrazine hydrate (1:1) → HCID 178505621, compound

HRID 1875444Notes

Reaction equation

HRID 1875444 reaction equation
Cl[C:2]1[C:7]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:19][NH2:20]>C(O)CCC.COC(C)(C)C>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:20][N:19]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59177869HCID 59177869, compound

Product 1

HCID 178505621HCID 178505621, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 2.00 g (8.01 mmol) of 1-(2-chloropyridin-3-yl)-2-(2-fluorophenyl)ethanone from example 11A and 560 mg (11.2 mmol) of hydrazine hydrate in 6 ml of 1-butanol is heated in a microwave at 200° C. for 10 min. It is then diluted with tert-butyl methyl ether, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. The solution is concentrated in vacuo. The crystalline residue is stirred with a little tert-butyl methyl ether and filtered off with suction. The mother liquor is concentrated and purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1). In total, 1.40 g (77% of theory) of the desired product are obtained as yellow crystals.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationThe solution is concentrated in vacuo
  4. filtrationfiltered off with suction
  5. concentrationThe mother liquor is concentrated
  6. custompurified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-92fbb16f0f0f491cb71514a71c63f453
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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