HCID 21889067, compound → HCID 21889077, compound

HRID 720210Notes

Reaction equation

HRID 720210 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)C.O.[Pd]>[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 21889067HCID 21889067, compound

Product 1

HCID 21889077HCID 21889077, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

40 g N-3-(morpholin4-yl)propyl-3-nitroaniline was dissolved in 450 ml ethanol and 50 ml water, and 0.5 Pd/C (5%) was added. After purging with nitrogen, hydrogenation was performed for 12 h at 50° C. under 50 bar of hydrogen pressure. After cooling, nitrogen purging was repeated, the catalyst was filtered off, and the filtrate was reduced in a rotary evaporator. 32.2 g of pasty black oil was obtained; this was distilled in a ball tube (220–232° C., 0.06–0.08 mbar). The product obtained was a crystalline orange material.

Workup

  1. customAfter purging with nitrogen, hydrogenation
  2. temperatureAfter cooling
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate was reduced in a rotary evaporator

Sources & evidence

ORD record
ord-f8ede97a614643d5817d8cdde4c92c8c
Source dataset
uspto-grants-2006_11
Patent number
US07135047B2

Reaction notes

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