Phosphorus oxide (P4O10) → 3,4-dihydro-5-methoxy-1(2H)-isoquinolinone

HRID 1843852

Reaction equation

HRID 1843852 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH2:6][NH:5][C:4]2=[O:3]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 68094307HCID 68094307, compound

Product 1

HCID 73850983,4-dihydro-5-methoxy-1(2H)-isoquinolinoneYield 12,697.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
110 °C

Procedure

Using the same procedure and workup as described in example 1, step 4, [2-(2-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester (I-13c: 0.9 g, 0.0040 mmol) in POCl3 (5 mL) was reacted with P2O5 (1.19 g, 0.0084 mmol). The resulting mixture was stirred at 110° C. for 3 hours to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 90 mg of the product (12.8% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-b77a98a8b3c04b15b6ba211da36e6f4a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Linked notes

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