Hydroxylamine → 2,4,N-trihydroxy-5-nitrobenzamide

HRID 643932Notes

Reaction equation

HRID 643932 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:15][OH:16].O>O1CCOCC1>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH:15][OH:16])=[O:5]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 866240182,4-Dihydroxy-5-nitrobenzoyl chloride

Product 1

HCID 866240192,4,N-trihydroxy-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,4-dihydroxy-5-nitrobenzoyl chloride (17.0 g, 78.1 mmol) in dioxane (70 mL) is added to an ice cold solution of 50% aqueous hydroxylamine (35 mL) and water (35 mL). After the addition is complete, the ice bath is removed and the mixture is stirred at room temperature for 30 min. The resulting thick precipitate is filtered, washed once with 1:1 water/dioxane and dried to obtain 2,4,N-trihydroxy-5-nitrobenzamide. After standing in the refrigerator for 18 h, the 1:1 water/dioxane solution affords additional 2,4,N-trihydroxy-5-nitrobenzamide: (M+H)+=215.1.

Workup

  1. additionAfter the addition
  2. customthe ice bath is removed
  3. filtrationThe resulting thick precipitate is filtered
  4. washwashed once with 1:1 water/dioxane
  5. customdried

Sources & evidence

ORD record
ord-7451c0f418a543ad859bd2aa406b2ed7
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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