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

HRID 375623Notes

Reaction equation

HRID 375623 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.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[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

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 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 1

HCID 12052TriethylsilaneSolvent2×

Procedure

To a solution of 1 g of 1,3-dichloro-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one in 30 mL of hot triethylsilane was added 5 m of trifluoroacetic acid and the mixture was stirred at 100° C.-110° C. under nitrogen. More triethylsilane and trifluoroacetic acid were added until the reaction was substantially complete as evidenced by TLC (basified aliquot extracted into CHCl3). Then all volatiles were removed in vacuo and the residue was basified, extracted into chloroform, and chromatographed using 20:1 chloroform:methanol on a silica gel column. Concentration of the corresponding fractions provided the desired 1,3-dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-ol as a greyish-white solid.

Workup

  1. extractionbasified aliquot extracted into CHCl3)
  2. customThen all volatiles were removed in vacuo
  3. extractionextracted into chloroform
  4. customchromatographed

Sources & evidence

ORD record
ord-16bb6bff7b6e4ddeb4b2e9c0f327781b
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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