Formic Acid → Olopatadine impurity 147

HRID 894185Notes

Reaction equation

HRID 894185 reaction equation
[C:1]([C:3]1[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.C(O)=[O:20]>[Ni]>[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:3]([CH:1]=[O:20])=[CH:4][C:5]1=2

Participants

4

Reactant 2

HCID 284Formic AcidHCID 124468252-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 12446833Olopatadine impurity 147

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Heat a mixture of 5.0 gm. of 2-cyano-6.11-dihydro-11-oxodibenz[b,e]oxepin and 4.0 gm. of Raney nickel alloy in 60 ml. of 75% (v/v) aqueous formic acid at reflux for 1.5 hours. Cool to room temperature and filter. Concentrate to small volume and extract with methylene chloride. Wash the extract with water and with 1 N sodium bicarbonate until neutral. Dry the neutral extract over sodium sulfate and concentrate to dryness to obtain the title product.

Workup

  1. temperatureHeat
  2. additiona mixture of 5.0 gm
  3. filtrationfilter
  4. concentrationConcentrate to small volume
  5. extractionextract with methylene chloride
  6. washWash the
  7. extractionextract with water and with 1 N sodium bicarbonate until neutral
  8. customDry the
  9. extractionneutral extract over sodium sulfate
  10. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-2a8e7d02ece34d5786073bf50b2ddd3f
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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