5-Chloro-2,4-dinitrobenzamide → HCID 18184366, compound

HRID 1358262Notes

Reaction equation

HRID 1358262 reaction equation
Cl[C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[O:17]1CCOCC1.CO>[OH-].[K+].Cl.O>[N+:11]([C:5]1[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([OH:17])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8])([O-:13])=[O:12]

Participants

6

Reactant 2

HCID 148972315-Chloro-2,4-dinitrobenzamideHCID 21966525Dioxane Methanol

Product 1

HCID 18184366HCID 18184366, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 5-chloro-2,4-dinitrobenzamide (5.50 g, 0.022 mmol) in p-dioxane/methanol (1:1, 120 mL) and 6N aqueous KOH (20 mL) is stirred at room temperature for 2 h. After acidification with concentrated HCl, the mixture is diluted with water and extracted into EtOAc. Workup gives 2,4-dinitro-5-hydroxybenzamide (4.91 g, 98%) as yellow cubes. 1H NMR (DMSO) δ8.64 (1H, s), 8.16 (1H, brs), 7.81 (1H, brs), 7.13 (1H, s), 5.80 (1H, brs).

Workup

  1. extractionextracted into EtOAc

Sources & evidence

ORD record
ord-d82e5b020cd4455da245823833e32a80
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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