Sulfuric Acid → HCID 15334806, compound

HRID 259733Notes

Reaction equation

HRID 259733 reaction equation
[CH:1]([C:4]([CH3:22])([N:7]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][C:15]3[CH:19]=[CH:18][N:17]([CH3:20])[C:16]=3[C:9]=2[C:8]1=[O:21])[C:5]#[N:6])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:24]>C(Cl)Cl>[CH:1]([C:4]([CH3:22])([N:7]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][C:15]3[CH:19]=[CH:18][N:17]([CH3:20])[C:16]=3[C:9]=2[C:8]1=[O:21])[C:5]([NH2:6])=[O:24])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22402978HCID 22402978, compound

Product 1

HCID 15334806HCID 15334806, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6,8-dihydro-α-isopropyl-α,1-dimethyl-6,8-dioxobenzo[2,1-b:3,4-c']dipyrrole-7(1H)-acetonitrile (5.30 g, 18.0 mmol) in methylene chloride is added dropwise to concentrated sulfuric acid at 5°-10° C. with rapid stirring. The ice bath is removed and the reaction mixture is stirred overnight at ambient temperatures, poured over crushed ice, diluted with methylene chloride, treated with 50% sodium hydroxide solution with ice bath cooling to pH 3-4 and separated. The aqueous layer is extracted with methylene chloride. The combined organic layers are dried (MgSO4) and concentrated in vacuo to give an orange foam residue, which is recrystallized from methylene chloride to afford the title product as yellow crystals (1.30 g, 23.2%), mp 184°-189° C.

Workup

  1. customThe ice bath is removed
  2. additionpoured
  3. customover crushed ice
  4. additiondiluted with methylene chloride
  5. additiontreated with 50% sodium hydroxide solution with ice bath
  6. temperaturecooling to pH 3-4
  7. customseparated
  8. extractionThe aqueous layer is extracted with methylene chloride
  9. dry with materialThe combined organic layers are dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customto give an orange foam residue, which
  12. customis recrystallized from methylene chloride

Sources & evidence

ORD record
ord-64d6f80ae3cd4ed9845107ac064d311d
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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