Hydrazine hydrate (1:1) → HCID 15626653, compound

HRID 628460Notes

Reaction equation

HRID 628460 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.O.[NH2:18][NH2:19].[Cl-].[NH4+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[NH:19][N:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 2805823HCID 2805823, compound

Product 1

HCID 15626653HCID 15626653, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-6-hydroxyhexane-1,3-dione (38 g, 0.17 mol) in 150 mL ethanol and hydrazine hydrate (17.05 g, 0.34 mol) is added slowly over a 30 min period (exothermic up to 35° C.). The resulting solution is stirred for 1 h at RT then the mixture is added to aqueous ammonium chloride. Extraction with ethyl acetate and evaporation of the organic phase results in the crude product. The product is purified by trituration with 2×200 mL n-hexane and the product is obtained as solid (29 g, 77%).

Workup

  1. extractionExtraction
  2. customwith ethyl acetate and evaporation of the organic phase
  3. customresults in the crude product
  4. customThe product is purified by trituration with 2×200 mL n-hexane

Sources & evidence

ORD record
ord-637e22e269c948c4a659fbe94630a5fd
Source dataset
uspto-grants-2016_04
Patent number
US09314026B2

Reaction notes

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