8-methoxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde → 2-[3-cyano-4-[2-(8-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo [ij]quinolizine-9-yl)vinyl]-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile

HRID 85318Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:14]2=[C:15]3[N:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]3=[CH:5][C:4]=1[CH:16]=O.[C:18]([C:20]1[C:21](=[C:28]([C:31]#[N:32])[C:29]#[N:30])[O:22][C:23]([CH3:27])([CH3:26])[C:24]=1[CH3:25])#[N:19]>C(O)C>[C:18]([C:20]1[C:21](=[C:28]([C:29]#[N:30])[C:31]#[N:32])[O:22][C:23]([CH3:26])([CH3:27])[C:24]=1[CH:25]=[CH:16][C:4]1[CH:5]=[C:6]2[C:15]3[N:10]([CH2:9][CH2:8][CH2:7]2)[CH2:11][CH2:12][CH2:13][C:14]=3[C:3]=1[O:2][CH3:1])#[N:19]

Participants

Conditions

Temperature: 50 °C

Procedure

In 5 ml of ethanol were dissolved 150 mg (0.65 mmol) of 8-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboaldehyde and 142 mg (0.71 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene)propanedinitrile. The mixture was stirred at room temperature for 3 hours and further at 50° C. for 3 hours. The precipitate was separated by filtration and washed with methanol. The crystal was purified by silica gel column chromatography and washed with methanol to give 228 mg of a dark blue crystal having amp of 250-252° C. (yield: 85.2%).

Workup

customThe precipitate was separated by filtration
washwashed with methanol
customThe crystal was purified by silica gel column chromatography
washwashed with methanol
customto give 228 mg of a dark blue crystal
customamp of 250-252° C. (yield: 85.2%)

Sources & evidence

ORD record: ord-747163de371a4142b2f6a7dd3e0c992e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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