HCID 21191818, compound → HCID 21191823, compound

HRID 1602126Notes

Reaction equation

HRID 1602126 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 11a) and 10 g of 5% Pt/C (platinum adsorbed on activated carbon) in 50 ml of methanol are stirred vigorously under a hydrogen blanket for 2 hours. A further 2 g of 5% Pt/C is added and the mixture is stirred overnight. The catalyst is filtered off and replaced by 10 g of fresh catalyst. The mixture is stirred overnight and suction filtered, and the filtrate is evaporated down under reduced pressure. The residue is purified by column chromatography with mixtures of hexane and ethyl acetate. There is obtained 61 g (0.286 mol=93%) of the title compound as a colorless solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. stirringThe mixture is stirred overnight
  3. filtrationsuction filtered
  4. customthe filtrate is evaporated down under reduced pressure
  5. customThe residue is purified by column chromatography with mixtures of hexane and ethyl acetate

Sources & evidence

ORD record
ord-a894a51d6db24bd98d14bc48339dbaf9
Source dataset
uspto-grants-1999_11
Patent number
US05981532

Reaction notes

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