Phosgene → HCID 12798644, compound

HRID 1284495Notes

Reaction equation

HRID 1284495 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:13](Cl)(Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl>[O:14]=[C:13]1[NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH:6]=[CH:7][CH:8]=[N:9][C:10]=3[C:11]=2[O:12]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 129094887-Aminoquinolin-8-ol

Product 1

HCID 12798644HCID 12798644, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 7-amino-8-hydroxyquinoline (3.2 g, 20.0 mmol) in methylene chloride (50 ml) was treated with 25 ml of 1.6M phosgene gas in methylene chloride. Triethylamine (12 ml) was slowly added and the reaction was stirred overnight. The reaction mixture was partially concentrated and water was added. After treating the resulting mixture with aqueous ammonium hydroxide a precipitate formed which was filtered and dried giving 3.4 g (91% yield) of solid. M.P. >300° C.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. additionwater was added
  3. additionAfter treating the resulting mixture with aqueous ammonium hydroxide a precipitate
  4. customformed which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-fd1f8cc4f13e422e86da3c6a40b4c198
Source dataset
uspto-grants-1986_01
Patent number
US04563463

Reaction notes

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