Nitroethane → 6-fluoro-5-methoxy-3-(2-nitro-propenyl)-1H-indole

HRID 1072612Notes

Reaction equation

[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[F:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:16]=O)=[CH:12][NH:13]2)=[CH:9][C:8]=1[O:18][CH3:19].C([O-])(=O)C.[NH4+]>>[F:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH3:5])=[CH:12][NH:13]2)=[CH:9][C:8]=1[O:18][CH3:19]

Participants

Reactant 3

HCID 6587Nitroethane

HCID 517165Ammonium Acetate

HCID 220148046-fluoro-5-methoxy-1H-indole-3-carbaldehyde

Product 1

HCID 695167926-fluoro-5-methoxy-3-(2-nitro-propenyl)-1H-indoleYield 92%

Conditions

Temperature: 100 °C

Procedure

A mixture of nitroethane(44 ml, 611 mmol), 6-fluoro-5-methoxy-1H-indole-3-carbaldehyde (11.8 g, 61 mmol), and ammonium acetate(1.78 g, 23 mmol) is stirred at 100° C. for 3 hours, allowed to cool, and is filtered to give 14 g of 6-fluoro-5-methoxy-3-(2-nitro-propenyl)-1H-indole (92%).

Workup

temperatureto cool
filtrationis filtered

Sources & evidence

ORD record: ord-94ba0eb600c54d3a88ed0030253e2cd8
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911463B2

Reaction notes

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