Phosphorus oxychloride → HCID 59626590, compound

HRID 1027269Notes

Reaction equation

HRID 1027269 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([CH3:19])[CH3:18])=[C:12]([O:20][CH3:21])[CH:11]=1)=O)=O.O=P(Cl)(Cl)Cl>C(#N)C>[CH:17]([O:16][C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][N:7]3[CH:1]=[N:3][CH:4]=[C:5]32)=[CH:11][C:12]=1[O:20][CH3:21])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86710683HCID 86710683, compound

Product 1

HCID 59626590HCID 59626590, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a 50 mL round bottom flask was added 2-formamido-N-(4-isopropoxy-3-methoxyphenethyl)acetamide (600 mg, 2.04 mmol) followed by acetonitrile (10.2 mL) and POCl3 (0.57 mL, 6.12 mmol). The reaction mixture was heated to 80° C. for one hour then concentrated in vacuo. To the resulting oil was added H2O and aqueous saturated sodium carbonate, then the solution was extracted with EtOAc (2×). The organic extracts were combined, dried with sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-10% MeOH in DCM) to afford 9-isopropoxy-8-methoxy-5,6-dihydroimidazo[5,1-a]isoquinoline (182 mg) MS [M+H+]=259.2.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionTo the resulting oil was added H2O and aqueous saturated sodium carbonate
  3. extractionthe solution was extracted with EtOAc (2×)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-311e680d7a6e42ea9f6233280cb9afe9
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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