Ammonia → Iniparib

HRID 2044212Notes

Reaction equation

HRID 2044212 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[NH3:15]>CO>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH2:15])=[O:2])=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 297884Methyl 4-iodo-3-nitrobenzoate

Product 1

HCID 9796068IniparibYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.5 mmol) in methanol (80 ml) is cooled to −15° C. To the solution, ammonia gas (about 1.02 g, 0.06 mol) is passed till saturation. The solution is kept at room temperature (25±2° C.) for 3 days. The solvent is then evaporated under reduced pressure to obtain 4-iodo-3-nitrobenzamide as an yellow solid (95% yield, 98% HPLC). The solid (1 g) is added to methanol (10 ml) and heated to 55° C. to get a clear solution. While the solution is hot, water (35 ml) is added and the precipitate so formed is filtered to obtain pure 4-iodo-3-nitrobenzamide.

Workup

  1. customis kept at room temperature
  2. custom(25±2° C.)
  3. customfor 3 days
  4. customThe solvent is then evaporated under reduced pressure

Sources & evidence

ORD record
ord-04bee67f05ee4bc5944156f7948c7658
Source dataset
uspto-grants-2013_11
Patent number
US08586792B2

Reaction notes

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