Ammonia → 4'-Chloro-2-hydroxy-4-methoxy-benzophenone imine

HRID 372287Notes

Reaction equation

HRID 372287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1.[NH3:19]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:19])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 665574'-Chloro-2-hydroxy-4-methoxybenzophenone

Product 1

HCID 1363884104'-Chloro-2-hydroxy-4-methoxy-benzophenone imine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 132 g. of 4'-chloro-2-hydroxy-4-methoxy-benzophenone in 500 ml. of methanol is cooled to -20° C. in a 2l. shaking autoclave and treated with 120 ml. of liquid ammonia. The mixture is then shaken at 120° C. for 20 hours under a nitrogen atmosphere. After cooling, the yellow crude product is filtered off under suction and washed with a small amount of methanol. There is obtained 4'-chloro-2-hydroxy-4-methoxy-benzophenone imine, having a melting point of 210°-212° C., which can be used in the next step without further purification. An analytical sample is obtained by recrystallization from methanol and has a melting point of 212°-214° C.

Workup

  1. additionA suspension of 132 g
  2. additiontreated with 120 ml
  3. stirringThe mixture is then shaken at 120° C. for 20 hours under a nitrogen atmosphere
  4. temperatureAfter cooling
  5. filtrationthe yellow crude product is filtered off under suction
  6. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-bab641742c94431b8a88403d69569ead
Source dataset
uspto-grants-1978_05
Patent number
US04089875

Reaction notes

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