Nitroethane → Ethyl 2-(3,5-dihydroxyphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydro-pyrrolo[2,1-a]-isoquinoline-1-carboxylate

HRID 585081Notes

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](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][CH2:7][CH2:6]2.[OH:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([OH:30])[CH:29]=1)[CH:25]=O.[N+]([CH2:34][CH3:35])([O-])=O.N1CCCCC1>C(O)C.C(O)(C)C.C(O)(C)C>[OH:21][C:22]1[CH:23]=[C:24]([C:25]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:9]3[C:10]4[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=4)[CH2:6][CH2:7][N:8]3[C:34]=2[CH3:35])[CH:27]=[C:28]([OH:30])[CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 500 mg (1.8 mmol) of ethyl (6,7-dimethoxy-3,4-dihydro-1(2H)-isoquinolinylidene)-ethanoate (Example III.1), 499 mg (3.61 mmol) of 3,5-dihydroxybenzaldehyde, 281 mg (3.61 mmol) of nitroethane and 61.4 mg (0.72 mmol) of piperidine in 10 mL of an ethanol/isopropanol 1:1 mixture was stirred at 80° C. overnight. 40 mL of isopropanol were added, the mixture was cooled to 0° C., and the resulting precipitate was filtered off. The solid was washed with ethanol and dried in vacuo to give the title compound as a white solid which was readily recrystallized from ethyl acetate to furnish white needles.

Workup

temperaturethe mixture was cooled to 0° C.
filtrationthe resulting precipitate was filtered off
washThe solid was washed with ethanol
customdried in vacuo

Sources & evidence

ORD record: ord-aa8fd636a9504701a856c152ff2eaebb
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930114B2

Reaction notes

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