Hydrochloric Acid → 4-Iodo-3-nitrobenzoic acid

HRID 1844777

Reaction equation

HRID 1844777 reaction equation
N[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.N([O-])=O.[Na+].[I-:19].[K+]>O>[I:19][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 23668193Sodium Nitrite

Product 1

HCID 112085984-Iodo-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

45 g (0.25 mol) 4-Amino-3-nitrobenzoic acid, 400 ml water and 100 ml concentrated hydrochloric acid were added into a reaction flask. Started to stir, and the mixture was cooled to 0 to 5° C., then 50 ml aqueous solution of 25.9 g sodium nitrite (0.38 mol) was added dropwise. The solid was dissolved gradually. After completing the dropwise addition, the mixture was reacted at 0 to 5° C. for 1 hour, and 200 ml aqueous solution of 88 g (0.5 mol) potassium iodide was added dropwise at this temperature. The mixture was stirred at room temperature for 2 h after completing the dropwise addition, and solid was precipitated. The solid was filtered, washed with water, and dried to obtain 4-iodo-3-nitrobenzoic acid (compound V) as a solid, 65 g (0.22 mol), yield 89.7%.

Workup

  1. dissolutionThe solid was dissolved gradually
  2. additionthe dropwise addition
  3. customthe mixture was reacted at 0 to 5° C. for 1 hour
  4. stirringThe mixture was stirred at room temperature for 2 h
  5. additionthe dropwise addition, and solid
  6. customwas precipitated
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-a77af131fd7f4975a52ff93caac551ac
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Linked notes

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