Nitric Acid → N-(4-Chloro-3-hydroxy-2-nitrophenyl)acetamide

HRID 2418637Notes

Reaction equation

HRID 2418637 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[OH:12].P(=O)(O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([N+:18]([O-:20])=[O:19])[C:3]=1[OH:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 14122483N-(4-Chloro-3-hydroxyphenyl)acetamide

Product 1

HCID 20444660N-(4-Chloro-3-hydroxy-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-30 °C

Procedure

0.23 mole (43 g) of 2-chloro-5-acetylamino phenol is dissolved, with agitation, in 500 cc of sulfuric acid (d=1.83) at a temperature of about +5° C. There are then added 15 cc of phosphoric acid and the resulting reaction medium is cooled to -30° C. There are then slowly added, over a 35 minute period, while vigorously agitating, 9.7 cc of nitric acid (d=1.52) in 1.5 cc of sulfuric acid (d=1.83). The reaction mixture is then poured over 3 kgs of shaved ice to precipitate the desired product which is separated by filtration, washed with water and dried, yielding 47 g of product.

Workup

  1. customthe resulting reaction medium
  2. additionThere are then slowly added, over a 35 minute period
  3. additionThe reaction mixture is then poured over 3 kgs of shaved ice
  4. customto precipitate the desired product which
  5. customis separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8834225c78984ef1924fbeb33eff8bc8
Source dataset
uspto-grants-1984_09
Patent number
US04473374

Reaction notes

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