Dimethylformamide diethylacetal → 3,4-dihydro-6,7-dimethoxy-2-(dimethylaminomethylene)-1(2H)-naphthalenone

HRID 1358997Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.C(O[CH:19](OCC)[N:20]([CH3:22])[CH3:21])C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[C:8](=[CH:19][N:20]([CH3:22])[CH3:21])[CH2:7][CH2:6]2

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone

Product 1

HCID 541518493,4-dihydro-6,7-dimethoxy-2-(dimethylaminomethylene)-1(2H)-naphthalenone

Procedure

The 3,4-dihydro-6,7-dimethoxy-2-(dimethylaminomethylene)-1(2H)-naphthalenone starting material was prepared from 6,7-dimethoxy-1-tetralone (4.12 g, 20 mmol) and N,N-dimethyl formamide diethyl acetal (10.3 ml, 60 mmol) to give the product as red-brown crystals (3.26 g) m.p. 138-140°. MS (ES+) 284 (MNa+, 12%), 262 (MH+, 100%), 189 (28%).

Sources & evidence

ORD record: ord-fc036b7ef48949d5a95b460d5db6b4d9
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599908B1

Reaction notes

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