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

HRID 1358989Notes

Reaction equation

HRID 1358989 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16].CO>C(Cl)Cl>[CH3:14][N:15]([CH:17]=[C:11]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]1=[O:10])[CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 107241-TetraloneHCID 78373Dimethylformamide dimethyl acetal

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3,4-dihydro-2-(dimethylaminomethylene)-1(2H)-naphthalenone starting material was prepared by heating a mixture of α-tetralone (5.85 g, 40 mmol) and N,N-dimethylformamide dimethyl acetal (32 ml, 240 mmol) at 110° for 3 h. The reaction was allowed to cool to room temperature and excess reagent removed in vacuo to give a thick oil. This crude material was subjected to column chromatography (silica, 5% methanol in CH2Cl2) to afford the desired product as a thick orange oil (3.50 g). δH (CDCl3) 8.02 (1 H, dd, J 7.7, 1.5 Hz), 7.72 (1 H, s), 7.36 (1 H, td, J 7.3, 1.6 Hz), 7.28 (1H, td, J 7.6, 1.5 Hz), 7.15 (1H, dm, J 7.3 Hz), 3.12 (6H, s) and 2.98-2.80 (4H, m). MS (ES+) 202 (MH+, 90%), 175 (MH+−HCN, 100%).

Workup

  1. temperatureby heating
  2. customexcess reagent removed in vacuo
  3. customto give a thick oil

Sources & evidence

ORD record
ord-5162c04f50a345a991c7b15ba87d1777
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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