HCID 20079497, compound → HCID 15053114, compound

HRID 1654060Notes

Reaction equation

HRID 1654060 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[N+:20]([O-])=O)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[NH2:20])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 20079497HCID 20079497, compound

Product 1

HCID 15053114HCID 15053114, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-acetyl-2,3-dihydro-N-(4-nitro-3-pyridinyl)-1H-indole-5-amine, N5 -oxide (13 g) in 250 ml ethanol containing 0.5 g PtO2 was hydrogenated for two days at 60 psi and thereafter filtered through Celite and concentrated to 9 g solid. This solid was purified by HPLC (silica, 20% methanol in ethyl acetate) to give 4 g solid. This was combined with 1 g product obtained from a previous reduction and again purified by HPLC (silica, 20% methanol in ethyl acetate) to give 5 g solid, m.p. 210°-212°. This solid was recrystallized from acetonitrile to give 4 g solid, m.p. 212°-214°.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated to 9 g solid
  3. customThis solid was purified by HPLC (silica, 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-3f9f89f984d74caebad26a49d16559d2
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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