Phosphorus oxide (P4O10) → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843844Notes

Reaction equation

HRID 1843844 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[CH3:15][O:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[C:4](=[O:3])[NH:5][CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 10822969Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 7.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

Using an analogous procedure and workup as described in Example 1, step 4, [2-(3-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester (I-11c: 6.2 g, 29.5238 mmol) in POCl3 (62 mL) was reacted with P2O5 (8.38 g, 59.047 mmol). The resulting mixture was stirred at 120° C. for 1 hour to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM) afforded 0.400 g of the product (7.6% yield).

Workup

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

Sources & evidence

ORD record
ord-535266f3ba3c480abfd79f2e07bdb8e4
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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