Hydrochloric Acid → 1,3-Dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-ol

HRID 375622Notes

Reaction equation

HRID 375622 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:18])[N:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:6]1=[N:7]2.Cl>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[CH:4]([OH:18])[N:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:6]1=[N:7]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10039448HCID 10039448, compound

Product 1

HCID 189925491,3-Dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2 g of 1,3-dichloro-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one in 100 mL of glacial acetic acid at 50° C. was added an intimately mixed mixture of 15 g zinc dust and 15 g silica gel (column chromatography grade). To this mechanically stirred suspension was added dropwise concentrated hydrochloric acid, while the progress of the reaction was followed by TLC (20:1 CHCl3 :MeOH, basified aliquots, extracted into chloroform). When the reaction was essentially complete, excess zinc was filtered off (pyrophoric!) the filtrate was concentrated in vacuo, basified, extracted with chloroform, and the crude extract was chromatographed using 20:1 chloroform:methanol as eluent on a silica gel column. The corresponding fractions after concentration in vacuo gave the 1,3-dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-ol as an off-white crystalline solid.

Workup

  1. extractionwhile the progress of the reaction was followed by TLC (20:1 CHCl3 :MeOH, basified aliquots, extracted into chloroform)
  2. filtrationexcess zinc was filtered off (pyrophoric!) the filtrate
  3. concentrationwas concentrated in vacuo
  4. extractionextracted with chloroform
  5. extractionthe crude extract
  6. customwas chromatographed
  7. concentrationThe corresponding fractions after concentration in vacuo

Sources & evidence

ORD record
ord-32976f6cca0941faa0a1b0639cd39fd1
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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