Ethyl trifluoroacetate → 1-Tetralone

HRID 1356882Notes

Reaction equation

HRID 1356882 reaction equation
N1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH2:6][CH2:5][C:4]=2C=N1.FC(F)(F)C(OCC)=[O:17].C[O-].[Na+]>CO>[C:9]1(=[O:17])[C:8]2[C:7](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 3398588HCID 3398588, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 107241-Tetralone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthetic Scheme III shows the procedure for preparation of 4,5-dihydrobenz[g]indazole compounds embraced by Formula I. In step 1, ethyl trifluoroacetate is reacted with base, such as 25% sodium methoxide in a protic solvent, such as methanol, and a 1-tetralone derivative (9) to give the intermediate diketone (10). In step 2, the diketone (10) in an anhydrous protic solvent, such as absolute ethanol or acetic acid, is treated with the free base or hydrochloride salt of a substituted hydrazine at reflux for 24 hours to afford a mixture of pyrazoles (11) and (12). Recrystallization gives the 4,5-dihydrobenz[g]indazolyl-benzenesulfonamide (11).

Sources & evidence

ORD record
ord-2d2eb2ca753b47a19ad8d6f099369593
Source dataset
uspto-grants-2003_07
Patent number
US06586603B1

Reaction notes

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