Dimethylformamide diethylacetal → 7-bromo-3,4-dihydro-2-dimethylaminomethylene-1-(2H)naphthalenone

HRID 1359016Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(O[CH:16](OCC)[N:17]([CH3:19])[CH3:18])C>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[CH:16][N:17]([CH3:19])[CH3:18])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 545338607-bromo-3,4-dihydro-2-dimethylaminomethylene-1-(2H)naphthalenone

Procedure

The 7-bromo-3,4-dihydro-2-dimethylaminomethylene-1-(2H)naphthalenone starting material was prepared from 7-bromo-3,4-dihydro-1(2H)-naphthalenone (9.0 g, 40.0 mmol) [Griffin, R W et al, J.O.C. (1964), 29, 2109] and N,N-dimethylformamide diethyl acetal (20.6 ml, 120.0 mmol) to give the product as yellow crystals (8.01 g) after recrystallisation from tert.butylmethyl ether. δH (CDCl3) 8.13 (1H, d, 2.2 Hz), 7.72 (1H, s), 7.45 (1H, dd, J 2.2, 8.0 Hz), 7.03 (1H, d, J 8.0 Hz), 3.13 (6H, s) and 2.92-2.74 (4H, m).

Sources & evidence

ORD record: ord-6dea265a42b74b2ebd4fde4a49e52011
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599908B1

Reaction notes

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