1,3-Cyclohexanedione → HCID 53751315, compound

HRID 1593627Notes

Reaction equation

HRID 1593627 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.Cl.[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1.O.C(O)C.C([O-])(=O)C.[Na+]>C(O)C.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH:18][C:1]2[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH:2]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 19096565Water ethanol

Product 1

HCID 53751315HCID 53751315, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared by a modification of a published procedure (Brueckner R. et al., European Patent EP 1 424 337 A1 (2004)). To a stirred solution of cyclohexane-1,3-dione (10 g, 0.089 mol) in ethanol (50 mL) and water (150 mL) was added portionwise under nitrogen over 15 minutes 4-fluorophenyl hydrazine hydrochloride (14.5 g, 0.089 mol). After 10 minutes 120 mL of 3:1 (v/v) water/ethanol was added in three portions. Solid sodium acetate (7.2 g) was then added portionwise over 45 minutes. The mixture was stirred for another 30 minutes at room temperature. The brown solid was collected, washed with 2×30 mL of 3:1 (v/v) water/ethanol and water, and dried in vacuo overnight to provide the title compound (16.48 g). MS (ES): [M+H]+ @m/z 221.1.

Workup

  1. customThe brown solid was collected
  2. washwashed with 2×30 mL of 3:1 (v/v) water/ethanol and water
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-bebf116a4bd84eedb77ba577252b85c1
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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