Phosphorus oxychloride → 1217472-10-0

HRID 1471343Notes

Reaction equation

HRID 1471343 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:14])=[N:8][NH:9][C:10]2=O)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([CH3:14])=[N:8][N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 576916797-methoxy-4-methyl-2H-phthalazin-1-one

Product 1

HCID 576916541217472-10-0Yield 100%

Conditions

Temperature
120 °C

Procedure

The solution of 7-methoxy-4-methyl-2H-phthalazin-1-one (3) in POCl3 (15 mL) is heated at reflux (120° C.) for 3 h 50 min and then cooled to room temperature. Unreacted POCl3 is removed at reduced pressure followed by azeotroping with toluene (2×10 mL). The residue is diluted with sat. NaHCO3 (60 mL) and extracted with dichloromethane (200 mL, 60 mL, and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is dried under high vacuum to give 2.08 g (100%) of 4 as a yellow solid, mp 151-153° C. IR 2968, 1613, 1218 cm−1; 1H NMR (CDCl3) δ 2.97 (s, 3H, CH3), 4.07 (s, 3H, CH3O), 7.50-7.59 (m, 2H, 6,8-PhthH), 8.01 ppm (d, J=8.7 Hz, 1H, 5-PhthH).

Workup

  1. temperaturecooled to room temperature
  2. customUnreacted POCl3 is removed at reduced pressure
  3. customby azeotroping with toluene (2×10 mL)
  4. additionThe residue is diluted with sat. NaHCO3 (60 mL)
  5. extractionextracted with dichloromethane (200 mL, 60 mL, and 50 mL)
  6. washThe extract is washed (brine)
  7. customdried
  8. customAfter solvent removal at reduced pressure
  9. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-bb1a5bcbafd442d0919d15faee2eced6
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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