Aniline → Aniline

HRID 1789250Notes

Reaction equation

HRID 1789250 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9].[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 7416NitrobenzeneHCID 7515N-Methylaniline

Product 3

HCID 6115AnilineHCID 7416NitrobenzeneHCID 66014N-Methyleneaniline

Conditions

Temperature
160 °C

Procedure

The procedure was the same as for Example 1 with the exception that aniline was omitted from the initial reaction solution. As the reactor contents heated to 160° C., approximately 30% of the nitrobenzene was converted. Complete nitrobenzene conversion required 5.5 hours at 160° C. and yielded 0.068 mole methyl N-phenyl carbamate (68% selectivity), 0.022 mole aniline, 0.007 mole N-methylene aniline, and 0.001 mole (N-methylaniline (summed to 30% selectivity to aniline).

Workup

  1. customreaction solution

Sources & evidence

ORD record
ord-c57a0c1cee394dc3b25d45365e2a55ac
Source dataset
uspto-grants-1987_08
Patent number
US04687872

Reaction notes

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