Reaction #1597002

ord-8c41e893f9694a3a8de50183059646fe

Reaction equation

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CCBr)cc1
4-nitrophenethyl bromide
→
O=C(O)c1cc(NCCc2ccc([N+](=O)[O-])cc2)ccc1O
5-(4-nitrophenethyl)aminosalicylic acid
Yield 90.3%

Reactants

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CCBr)cc1
4-nitrophenethyl 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 (500 mg, 3.26 mmole) and 4-nitrophenethyl bromide (900 mg, 3.92 mmole), 890 mg (50% yield) of 5-(4-nitrophenethyl)aminosalicylic acid was obtained as a pale yellow solid.:mp 234-236° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08211877B2uspto-grants-2012_07