Reaction #1597004

ord-56dc57cadedb44788aa45984c17404d6

Reaction equation

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CBr)cc1
4-nitrobenzyl bromide
→
O=C(O)c1cc(NCc2ccc([N+](=O)[O-])cc2)ccc1O
5-(4-nitrobenzyl)aminosalicylic acid
Yield 79.0%

Reactants

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CBr)cc1
4-nitrobenzyl bromide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherin Synthesis Example 1

Procedure

By following the similar procedure in Synthesis Example 1 by using 5-aminosalicylic acid (2.00 g, 13.0 mmole) and 4-nitrobenzyl bromide (3.38 g, 15.6 mmole), 2.90 g (79% yield) of 5-(4-nitrobenzyl)aminosalicylic acid was obtained as a pale yellow solid.: mp 211-212° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08211878B2uspto-grants-2012_07