Permanganate → HCID 19094234, compound

HRID 487180Notes

Reaction equation

HRID 487180 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[Mn]([O-])(=O)(=O)=O.FC1C=C(C)C=CC=1[N+:26]([O-])=O.[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]N>C1(C)C=CC=CC=1>[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][C:2]1[C:3]([NH2:26])=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 24401PermanganateHCID 666482-ChlorobenzylamineHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 19094234HCID 19094234, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Example 1(ii) was followed. From 6.25 g (33.8 mmol) of 3-fluoro-4-nitrobenzoic acid (mp 168°-169° C.; prepared by the method of F. C. Schmelkes and M. Rubin, J.A.C.S., 66, 1631 (1944), by permanganate oxidation of 3-fluoro-4-nitrotoluene) 11.96 g (84.5 mmol) of 2-chlorobenzylamine and 100 mL of toluene refluxed for 24 hours was obtained, after workup and crystallization from methanol, 8.4 g (82%) of 3-[(2-chlorophenyl)methyl]-amino-4-nitrobenzoic acid; mp 221°-223° C.

Workup

  1. customprepared by the method of F
  2. customwas obtained
  3. customafter workup and crystallization from methanol, 8.4 g (82%) of 3-[(2-chlorophenyl)methyl]-amino-4-nitrobenzoic acid

Sources & evidence

ORD record
ord-2c3ce37f0cca4d039d0c47b19f543e0e
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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