Dimethylformamide diethylacetal → HCID 54533860, compound

HRID 1106570Notes

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 54533860HCID 54533860, compound

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-b0062974edc94e2caf849af4baa707f6
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057329

Reaction notes

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