Phosphorus oxychloride → HCID 86664561, compound

HRID 1620403Notes

Reaction equation

HRID 1620403 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14](=O)[NH:15][N:16]=[CH:17][C:18]=2[N:19]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:14]1[C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[N:19][C:18]=2[CH:17]=[N:16][N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67491485HCID 67491485, compound

Product 1

HCID 86664561HCID 86664561, compound

Conditions

Temperature
100 °C

Procedure

A heterogeneous mixture of 2-(2,4-difluorophenylamino)pyrido[3,2-d]pyridazin-5(6H)-one (1.08 g, 3.9 mmol) and phosphorus oxychloride (10.00 mL, 39 mmol) was heated at 100° C. for 1.5 h. The excess POCl3 was removed on the rotovap and the crude residue was treated with ice cold 1N NaOH. The precipitated solid was filtered, rinsed with 2×5 mL of water followed by 2×5 mL of ether, and dried in a vacuum oven at 45° C. for 18 h to provide 5-chloro-N-(2,4-difluorophenyl)pyrido[3,2-d]pyridazin-2-amine as a tan solid. MS (ESI, pos.ion) m/z: M+1=293.0

Workup

  1. customThe excess POCl3 was removed on the rotovap
  2. additionthe crude residue was treated with ice cold 1N NaOH
  3. filtrationThe precipitated solid was filtered
  4. washrinsed with 2×5 mL of water
  5. customdried in a vacuum oven at 45° C. for 18 h

Sources & evidence

ORD record
ord-8ead3ae4e22640a4b772f26fadbc95aa
Source dataset
uspto-grants-2014_07
Patent number
US08772481B2

Reaction notes

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