Hydrochloric Acid → (2-Chlorophenyl)(2-nitrophenyl)methanone

HRID 725665Notes

Reaction equation

HRID 725665 reaction equation
N[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])=[O:5].[ClH:19].N([O-])=O.[Na+]>O>[Cl:19][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14903636HCID 14903636, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19708250(2-Chlorophenyl)(2-nitrophenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 75 g. of 2-amino-2'- nitrobenzophenone in 700 ml. of hot concentrated hydrochloric acid is cooled to 0° and a solution of 21.5 g. of sodium nitrite in 50 ml. of water is added in the course of 3 hours. The temperature of the suspension is kept at 2-7° during the addition. The resulting clear solution is poured into a stirred solution of 37 g. of cuprous chloride in 350 ml. of hydrochloric acid 1:1. The solid which has formed after a few minutes is filtered off, washed with water and recrystallized from ethanol. Crystals of 2-chloro-2'-nitrobenzophenone melting at 76-79° are obtained.

Workup

  1. additionThe temperature of the suspension is kept at 2-7° during the addition
  2. additionThe resulting clear solution is poured into a stirred solution of 37 g
  3. customThe solid which has formed after a few minutes
  4. filtrationis filtered off
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6b5c5783decf4b0588656c979c3e6905
Source dataset
uspto-grants-1998_01
Patent number
US05706829

Reaction notes

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