HCID 21889081, compound → HCID 21889071, compound

HRID 720208Notes

Reaction equation

HRID 720208 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)C.O.[Pd]>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 21889081HCID 21889081, compound

Product 1

HCID 21889071HCID 21889071, compoundYield 74.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20 g N-2-(morpholin4-yl)ethyl-3-nitroaniline was dissolved in 270 ml ethanol and 30 ml water, and 0.3 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 on a rotary evaporator. 13.2 g of black oil was obtained; this was distilled twice in a ball tube (180–206° C., 0.06–0.08 mbar). The product obtained was a viscous orange oil (middle fraction).

Workup

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

Sources & evidence

ORD record
ord-0b2107269be34407839419bb0165aeed
Source dataset
uspto-grants-2006_11
Patent number
US07135047B2

Reaction notes

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