Phosphorus oxychloride → HCID 57842568, compound

HRID 735541Notes

Reaction equation

[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([F:19])[CH:18]=1)[C:15](=O)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:15]1[C:16]2[C:11](=[CH:10][C:9]([N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][C:17]=2[F:19])[CH:12]=[CH:13][N:14]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 598380236-(Dibenzylamino)-8-fluoroisoquinolin-1(2H)-one

Product 1

HCID 57842568HCID 57842568, compoundYield 89%

Conditions

Temperature: 100 °C

Procedure

A mixture of 19D (0.622 g, 1.74 mmol) and phosphorous oxychloride (6 mL) was heated at 100° C. for 1.5 h. The reaction mixture was concentrated under reduced pressure and co-evaporated twice with toluene. Ice was added to the residue, followed by sodium hydroxide (1N solution) until the pH was basic. The mixture was extracted with methylene chloride (3×), and the combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried (MgSO4), and dried in vacuo to give 19E (0.583 g, 89%) as a yellow solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionIce was added to the residue
extractionThe mixture was extracted with methylene chloride (3×)
washthe combined organic layers were washed with saturated sodium bicarbonate solution and brine
dry with materialdried (MgSO4)
customdried in vacuo

Sources & evidence

ORD record: ord-ec096b94773446cfbc05c7f61c1c2903
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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