Potassium Carbonate → HCID 9966834, compound

HRID 1372535Notes

Reaction equation

HRID 1372535 reaction equation
[NH2:1][C:2]1[C:3]([Br:20])=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[C:6]([CH2:18][CH3:19])([CH2:12][CH2:13][C:14](=[O:17])[CH2:15][CH3:16])[CH2:5]2.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.Cl.CCOC(C)=O>[NH2:1][C:2]1[C:3]([Br:20])=[C:4]2[C:8]([C:7]3[C:6]([CH2:18][CH3:19])([CH2:5]2)[CH2:12][CH2:13][C:14](=[O:17])[C:15]=3[CH3:16])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 179727525-Amino-4-bromo-2-ethyl-2-(3-oxopentyl)-1-indanone

Product 1

HCID 9966834HCID 9966834, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The crude diketone (1.17 g) from step 3 was dissolved in acetic acid (14 mL) and the solution was diluted with aqueous 6N HCl (14 mL). The resulting mixture was stirred and heated in an oil bath at 80° C. for 5 hours and then kept at room temperature for 3 days. The mixture was diluted with EtOAc (100 mL) and carefully basified with aqueous K2CO3 (200 mL). The organic portion was washed with brine, dried over MgSO4 filtered, and evaporated under vacuum. The residue was lyophilized from benzene to afford crude 7-amino-8-bromo-9a-ethyl-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (1.0 g) as an amorphous solid.

Workup

  1. washThe organic portion was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-20a3673fac2b4d139bf8f92dcf078356
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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