Diazomethane → HCID 12813954, compound

HRID 1076506Notes

Reaction equation

HRID 1076506 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]([OH:18])=[O:17])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[N+](=[CH2:21])=[N-]>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]([O:18][CH3:21])=[O:17])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 12813951HCID 12813951, compound

Product 1

HCID 12813954HCID 12813954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.9 gm of 2-chloro-9-carboxy-acridine were suspended in 5 cc of methylene chloride at room temperature and then 60 cc of a methylene chloride solution of diazomethane titrating 17.9 gm per liter was added thereto. The reaction mixture was then stirred for 90 minutes while bubbling nitrogen therethrough to eliminate excess diazomethane. The methylene chloride solution was washed with an aqueous solution of 10% sodium carbonate, then with water, dried over magnesium sulfate, treated with charcoal, filtered and then evaporated to dryness. The residue was recrystallized from boiling methanol to obtain 3.2 gm of 2-chloro-9 -methoxycarbonylacridine melting at 130°C. The product occurred as a pale yellow solid soluble in chloroform, slightly soluble in ether and alcohol and insoluble in water.

Workup

  1. customwhile bubbling nitrogen
  2. washThe methylene chloride solution was washed with an aqueous solution of 10% sodium carbonate
  3. dry with materialwith water, dried over magnesium sulfate
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was recrystallized

Sources & evidence

ORD record
ord-94c25740e8e54c049f3c5595b0983325
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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