HCID 15053101, compound → HCID 15053115, compound

HRID 703493Notes

Reaction equation

HRID 703493 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)([O-])=O>C(O)C.[Pd]>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[NH2:1])=[CH:19][CH:18]=2)[CH:14]=[CH:15]1

Participants

4

Reactant 1

HCID 15053101HCID 15053101, compound

Product 1

HCID 15053115HCID 15053115, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of 10% Pd/C (1.0 g) in 10 ml of ethanol was added 5-[(3-nitro-4-pyridinyl)oxy]-1H-indole (3.7 g) in 240 ml ethanol and this was shaken on a Parr apparatus for 1 hour. The mixture was filtered and the filtrate concentrated to yield an oil (3.1 g) which was eluted with ethyl acetate on a silica gel column via HPLC. The desired fractions were concentrated to an oil which solidified on standing to yield 2.6 g, m.p. 155°-157° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f621a9db3e5c4b48afc827b50e1e170c
Source dataset
uspto-grants-1991_01
Patent number
US04983615

Reaction notes

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