HCID 21191818, compound → HCID 21191823, compound

HRID 1421375Notes

Reaction equation

HRID 1421375 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O>CO.[Pt]>[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12]

Participants

4

Reactant 1

HCID 21191818HCID 21191818, compound

Product 1

HCID 21191823HCID 21191823, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 887MethanolSolvent

Procedure

75 g (0.308 mol) of 2-(2'-methylphenoxymethyl)nitrobenzene (Example 2a) and 10 g of 5% strength Pt/C (platinum adsorbed onto active carbon) in 50 ml of methanol are stirred vigorously for two hours under an H2 atmosphere. Thereafter, a further 2 g of 5% strength Pt/C are added and stirring is continued overnight. The catalyst is then filtered off under suction and is replaced with 10 g of fresh catalyst. Stirring is continued overnight, the mixture is filtered under suction and the filtrate is evaporated down under reduced pressure. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 61 g (0.286 mol=93%) of the title compound are obtained as a colorless solid.

Workup

  1. filtrationThe catalyst is then filtered off under suction
  2. stirringStirring
  3. waitis continued overnight
  4. filtrationthe mixture is filtered under suction
  5. customthe filtrate is evaporated down under reduced pressure
  6. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-a57ff8148031445e8a10b1572f544edd
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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