Phosphorus oxychloride → HCID 86643480, compound

HRID 1423357Notes

Reaction equation

HRID 1423357 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:21]>>[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:13]2[C:4](=[C:5]([Cl:21])[N:6]=[C:7]3[C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68668559HCID 68668559, compound2×

Product 1

HCID 86643480HCID 86643480, compound

Conditions

Temperature
80 °C

Procedure

To the product from Step 3, 8-bromo-9-methoxy-1,3,4,5-tetrahydrophenanthridin-6(2H)-one (880 mg, 2.86 mmol) was added POCl3 (6 mL, 64.4 mmol) and the mixture was heated to 80° C. for 3 h. The excess POCl3 was then removed in vacuo, the residue was dissolved in DCM and the pH was adjusted to 5 with 1N NaOH. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo. The resulting solid was tritrated with ether to yield the title compound as a light yellow solid. LRMS (M+H)+=325.8.

Workup

  1. customThe excess POCl3 was then removed in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-93733c070a2745ce913c93edbec8756c
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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