Acetic Acid → Olopatadine Impurity 17

HRID 894168Notes

Reaction equation

HRID 894168 reaction equation
C(C1[CH:18]=[CH:17][C:6]2[O:7][CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:5]=2[CH:4]=1)#N.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>O>[O:12]=[C:11]1[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[CH2:8][O:7][C:6]2[CH:17]=[CH:18][C:21]([C:20]([OH:23])=[O:22])=[CH:4][C:5]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 124468252-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 12446821Olopatadine Impurity 17

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux 27.3 gm. of 2-cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin in a mixture of 300 cc. of 37% aqueous hydrochloric acid and 300 cc. of glacial acetic acid for 24 hours. Cool, dilute with water and separate the solids by filtration in order to obtain the title product (m.p. 250° C. dec.).

Workup

  1. temperatureReflux 27.3 gm
  2. temperatureCool
  3. customseparate the solids
  4. filtrationby filtration in order

Sources & evidence

ORD record
ord-22b50447770248b19f472dbeb7d6785f
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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