HCID 19816100, compound → HCID 10176695, compound

HRID 2247859Notes

Reaction equation

HRID 2247859 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

3

Reactant 1

HCID 19816100HCID 19816100, compound

Product 1

HCID 10176695HCID 10176695, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,3-dihydro-1-(4-nitro-3-pyridinyl)-1H-indole, N-oxide (4.5 g) in 250 ml ethanol containing 0.5 g platinum oxide was hydrogenated at 50 psi (pounds per square inch) for five hours and thereafter filtered and concentrated to an oil. This oil was purified by flash chromatography (silica, 10% methanol in dichloromethane) to give 4 g oil. This oil was converted to the hydrochloride salt and recrystallized twice from ethanol/ether to give 3 g crystals, d 274°.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to an oil
  3. customThis oil was purified by flash chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c2aa13fc1014249b4d558da23f14093
Source dataset
uspto-grants-1991_08
Patent number
US05037835

Reaction notes

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