Ethanol → HCID 86744474, compound

HRID 1654066Notes

Reaction equation

HRID 1654066 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1F)([O-:3])=[O:2].[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[C:16]2[CH3:23].C([OH:26])C>>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH+:12]([O-:26])[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[C:16]2[CH3:23])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 2586882,3-dimethyl-1H-indol-5-amineHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 86744474HCID 86744474, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 4-nitro-3-fluoropyridine N-oxide (4.2 g) and 5-amino-2,3-dimethylindole (4.2 g) in 100 mL of thoroughly degassed absolute ethanol was stirred at 50° C. for 30 minutes and then cooled slowly to 0° C. The precipitate was collected and air dried to give 7.3 g of N-(4-nitro-3-pyridinyl)-2,3-dimethyl-1H-indol-5-amine N5 -oxide as a powder. This powder was taken up in 225 mL of isopropanol and hydrogenated at 50° C. over 3% platinum on carbon at 50 psi in the presence of lithium hydroxide (0.21 g). Filtration and concentration left 4.7 g of a solid which was recrystallized twice from methanol giving 2.4 g of crystals. This material was then azeotroped repeatedly with absolute ethanol and dried at 85° to give 1.4 g of crystals, mp=112°-115° C.

Workup

  1. temperaturecooled slowly to 0° C
  2. customThe precipitate was collected
  3. customair dried

Sources & evidence

ORD record
ord-bb52b7279a654ce082ef33d4b589501b
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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