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

HRID 1633353Notes

Reaction equation

HRID 1633353 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-36b4136fe9114308ab4ac87295925f59
Source dataset
uspto-grants-1984_10
Patent number
US04480100

Reaction notes

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