1-Tetralone → 2-dimethylaminomethylene-3,4-dihydro-2H-naphthalen-1-one

HRID 2063775Notes

Reaction equation

HRID 2063775 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:12][N:13]([CH:15](OC)OC)[CH3:14].CC(OC(N(C)C)N(C)C)(C)C>CC#N>[CH3:12][N:13]([CH:15]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 78373Dimethylformamide dimethyl acetalHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 544065092-dimethylaminomethylene-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3,4-dihydro-2H-naphthalen-1-one in MeCN and 20 eq. of DMF-DMA were stirred at 90° C. overnight. Thin layer chromatography indicated there is almost no desired product, hence 1.2 equivalents of Bredereck's reagent was added, and the reaction mixture stirred at 80° C. overnight. The solvent was removed under reduced pressure and the crude material material was used for the next step with no further purification.

Sources & evidence

ORD record
ord-301eb186f81544c793e9532eb54453b8
Source dataset
uspto-grants-2012_10
Patent number
US08288400B2

Reaction notes

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