Reaction #1597012

ord-61e980915eb64b168dfa2c8be17ada49

Reaction equation

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CCCBr)cc1
3-(4-nitrophenyl)propyl bromide
→
O=C(O)c1cc(NCCCc2ccc([N+](=O)[O-])cc2)ccc1O
5-[3-(4-nitrophenyl)-n-propyl]aminosalicylic acid
Yield 50.4%

Reactants

Nc1ccc(O)c(C(=O)O)c1
5-aminosalicylic acid
O=[N+]([O-])c1ccc(CCCBr)cc1
3-(4-nitrophenyl)propyl 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 3-(4-nitrophenyl)propyl bromide (950 mg, 3.92 mmole), 520 mg (50% yield) of 5-[3-(4-nitrophenyl)-n-propyl]aminosalicylic acid was obtained as a pale yellow solid.: mp 229-231° C.

Source

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