Hydrochloric Acid → [2-[(3-Nitro-2-pyridinyl)amino]phenyl]phenylmethanone hydrochloride

HRID 463019Notes

Reaction equation

HRID 463019 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1.Cl.CCCCCC>C(Cl)Cl>[ClH:16].[N+:23]([C:22]1[C:17]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[N:18][CH:19]=[CH:20][CH:21]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 760802-AminobenzophenoneHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 70409212[2-[(3-Nitro-2-pyridinyl)amino]phenyl]phenylmethanone hydrochlorideYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 56.0 g (0.28 mole) of 2-aminobenzophenone and 49.6 g (0.31 mole) of 2-chloro-3-nitropyridine was heated in an oil bath with stirring at 150° C. for 45 minutes. After cooling, an 8.7 g portion of the product was dissolved in 45 ml of methylene chloride, hydrogen chloride gas was added for 15 min and 100 ml of hexane was added. After stirring for 20 min, solid was collected and washed twice with 1:3 mixture of methylene chloride to hexanes. After drying in air, 8.2 g (81.6%) product was obtained.

Workup

  1. temperaturewas heated in an oil bath
  2. temperatureAfter cooling
  3. stirringAfter stirring for 20 min
  4. customsolid was collected
  5. washwashed twice with 1:3 mixture of methylene chloride to hexanes
  6. customAfter drying in air

Sources & evidence

ORD record
ord-76ecb26e72db4a58b45b12d4356ecd64
Source dataset
uspto-grants-1985_05
Patent number
US04518603

Reaction notes

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