Ethanol → HCID 86744472, compound

HRID 1654064Notes

Reaction equation

HRID 1654064 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])=[CH:16]2.C([OH:25])C>>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH+:12]([O-:25])[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[CH:16]2)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olateHCID 27339925-Amino-2-methylindole

Product 1

HCID 86744472HCID 86744472, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 4-nitro-3-fluoropyridine N-oxide (5.4 g) and 5-amino-2-methylindole (5.0 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 9.0 g of N-(4-nitro-3-pyridinyl)-2-methyl-1H-indol-5-amine N5 -oxide as a powder. This powder was taken up in 135 mL of isopropanol and hydrogenated at 50° C. over 3% platinum on carbon at 50 psi in the presence of lithium hydroxide (0.26 g). Filtration and concentration left 8.0 g of a solid which was recrystallized from 32 mL of methanol giving 4.9 g of crystals. This material was then azeotroped repeatedly with absolute ethanol and dried at 85° C. to give 2.4 g of crystals, mp=96°-98° C.

Workup

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

Sources & evidence

ORD record
ord-851ff3b8d6024d08b8d364c61d5ef1ec
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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