5-Chloro-2-nitrobenzoic acid → HCID 59238177, compound

HRID 2068570Notes

Reaction equation

HRID 2068570 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[NH:14]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>OS([O-])(=O)=O.[K+]>[N:14]1([C:2]2[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 172865-Chloro-2-nitrobenzoic acidHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 59238177HCID 59238177, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 516920Potassium bisulfateSolvent

Conditions

Temperature
110 °C

Procedure

5-Chloro-2-nitro-benzoic acid (42.3 g) and homopiperizine (100 g, 4.8 eq.) were mixed without solvent and heated at 110° C. After 10 min, the mixture had melted into an orange, thick solution. After 45 min total reaction time, the mixture turned to a dark black-brown color and become very thick. At this time, the mixture was cooled to room temperature and diluted with 10% KHSO4 (wt/vol) aqueous solution (pH 4). This mixture was stirred at room temperature for ˜1 hour and then filtered. The solid was rinsed with a mixture of hexanes and diethyl ether, diethyl ether and then hexane. The solid was then dried under vacuum. This resulted in 40.8 g (73%) of a dark brown solid. The compound was carried on to the next step without further analysis or purification.

Workup

  1. waitAfter 45 min total reaction time
  2. temperatureAt this time, the mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe solid was rinsed with a mixture of hexanes and diethyl ether, diethyl ether
  5. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-718e50b6542747d8b875b3b5f7f2e2a7
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

Loading…