Acetic Acid → HCID 13067121, compound

HRID 1388617Notes

Reaction equation

HRID 1388617 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Cl:7][C:8]1[CH:30]=[CH:29][C:11]2[C:12]3[C:13](=[C:24]([CH:27]=[O:28])[NH:25][CH:26]=3)[CH2:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:10]=2[CH:9]=1.C(O)(=[O:33])C>CC(C)=O.S(=O)(O)[O-].[Na+]>[Cl:7][C:8]1[CH:30]=[CH:29][C:11]2[C:12]3[C:13](=[C:24]([C:27]([OH:33])=[O:28])[NH:25][CH:26]=3)[CH2:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 13067120HCID 13067120, compound

Product 1

HCID 13067121HCID 13067121, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 23665763Sodium BisulfiteSolvent

Procedure

A solution of 1.5 g (9.5 mmol) of potassium permanganate in 150 ml of 50% aqueous acetone was added dropwise to a solution of 1.6 g (4.5 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine-3-carboxaldehyde in 100 ml of acetone. After 2.5 hr the mixture was diluted with a saturated aqueous solution of sodium bisulfite, neutralized with the addition of acetic acid and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. Trituration of the residue with methylene chloride gave yellow crystals, mp 216°-218°. Recrystallization from a mixture of ethanol and ether gave yellow prisms, mp 252°-254° (dec).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to dryness
  4. customTrituration of the residue with methylene chloride gave yellow crystals, mp 216°-218°
  5. customRecrystallization
  6. additionfrom a mixture of ethanol and ether
  7. customgave yellow prisms, mp 252°-254° (dec)

Sources & evidence

ORD record
ord-cb0c184892ac41c0876f68c5ab76413a
Source dataset
uspto-grants-1984_02
Patent number
US04431823

Reaction notes

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