2-Nitrotoluene → N-Hydroxy-2-toluidine

HRID 1383747Notes

Reaction equation

HRID 1383747 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-])=[O:2].C(N)CC>C1(C)C=CC=CC=1.[Pt]>[C:5]1([CH3:10])[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:1][OH:2]

Participants

5

Reactant 2

HCID 69442-NitrotolueneHCID 7852Propylamine

Product 1

HCID 11908N-Hydroxy-2-toluidine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
6.5 °C

Procedure

41.1 g (0.3 mol) of o-nitrotoluene in 600 ml of toluene were initially taken with 5.1 g of active carbon, with stirring, in a 1.5 l hydrogenation flask having a gas inlet tube. After cooling to about 5-8° C., 67.4 g (1.1 mol) of n-propylamine and 3 g of platinum on carbon (5%) (CF 105 XRS from Degussa) were added and the reaction vessel was flushed at 5° C. with nitrogen and then with hydrogen. The hydrogenation was carried out at a constant hydrogen pressure of 100 mbar gauge pressure. According to HPLC analysis, the reaction was complete after 100 minutes.

Workup

  1. customthe reaction vessel was flushed at 5° C. with nitrogen

Sources & evidence

ORD record
ord-6744df4e26614d4f963da38bf55b8c46
Source dataset
uspto-grants-2001_07
Patent number
US06255489B1

Reaction notes

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