Hydrochloric Acid → 2-Chloro-5-nitrophenol

HRID 1252021Notes

Reaction equation

HRID 1252021 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].N([O-])=O.[Na+].S(=O)(=O)(O)N.N(O)=O.[ClH:24]>>[Cl:24][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 5987Sulfamic AcidHCID 24529Nitrous AcidHCID 49847212-Amino-5-NitrophenolHCID 23668193Sodium Nitrite

Product 1

HCID 692642-Chloro-5-nitrophenol

Procedure

A suspension of 131.2 g (0.85 mole) of 2-amino-5-nitrophenol in 400 ml of 36% hydrochloric acid was maintained at a temperature of 10° C. or less with stirring. To this was added dropwise 150 ml of an aqueous solution containing 66.5 g (0.93 mole) of sodium nitrite over a period of about 1 hour. After completion of the dropwise addition, the mixture was further stirred at a temperature not exceeding 10° C. for 1 hour. To this mixture was added 3 g of sulfamic acid to decompose the excess nitrous acid. The suspension was added to 100 ml of a 20% hydrochloric acid aqueous solution containing 17 g of cuprous chloride with stirring. The stirring was continued for 1 hour.

Workup

  1. temperaturewas maintained at a temperature of 10° C. or less
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was further stirred at a temperature not
  4. stirringwith stirring
  5. waitThe stirring was continued for 1 hour

Sources & evidence

ORD record
ord-6307c30870d04569b21ca6ced8351c47
Source dataset
uspto-grants-1988_05
Patent number
US04741997

Reaction notes

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