Ammonium Hydroxide → HCID 59256606, compound

HRID 640802Notes

Reaction equation

HRID 640802 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([OH:12])=[C:7]([N+:13]([O-:15])=[O:14])[C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH4+:20].[OH-]>C1(C)C=CC=CC=1>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]([C:4]([NH2:20])=[O:5])=[C:7]([N+:13]([O-:15])=[O:14])[C:8]=1[OH:12]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 59256606HCID 59256606, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,4-dichloro-5-hydroxy-6-nitrobenzoic acid (Step A) (4.40 g, 17.6 mmol) and thionyl chloride (2 mL, 27 mmol) in toluene (60 mL) was heated under reflux for 1 h and allowed to cool to room temperature. The solution was added to conc NH4OH (40 mL) at 0° C. The cooling bath was removed and the mixture stirred at room temperature for 2 h and then concentrated to give crude 4,6-dichloro-3-hydroxy-2-nitrobenzamide as a brown solid.—1H NMR (CD3OD): δ 7.33 (s, 1H); mass spectrum: m/z 249, 251, 253 (M+−1, 100%, 66%, 11%).

Workup

  1. temperatureunder reflux for 1 h
  2. customThe cooling bath was removed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2c947222660045819d02c5ef75c3b79a
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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