Water → HCID 21082066, compound

HRID 346981Notes

Reaction equation

HRID 346981 reaction equation
S(=O)(=O)(O)[OH:2].[OH2:6].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:25]#N)[CH:22]=3)[N:17]3[N:34]=[N:35][N:36]=[C:16]3[CH:15]=2)[CH:11]=[CH:12][CH:13]=1>C(O)(=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:25]([OH:2])=[O:6])[CH:22]=3)[N:17]3[N:34]=[N:35][N:36]=[C:16]3[CH:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 21082067HCID 21082067, compound

Product 1

HCID 21082066HCID 21082066, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuric acid (25 ml) was added slowly to H2O (25 ml). Acetic acid (25 ml) was added. Intermediate (59) (0.0190 mol) was added portionwise. The mixture was stirred and refluxed for 18 hours then cooled, poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue (8.9 g) was taken up in EtOAc. The organic layer was separated, washed several times with water, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 7.8 g (91%) of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-tetrazolo[1,5-a]quinoline-7-acetic acid, MS (ESI) m/z:449, 451, 453 (MH+) (intermediate 60).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperaturethen cooled
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness
  8. customThe organic layer was separated
  9. washwashed several times with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-e173a43c013844d89ef3beca213d3738
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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