Phosphorus oxide (P4O10) → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843888Notes

Reaction equation

HRID 1843888 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][NH:5][C:4]2=[O:3])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 887923HCID 887923, compound

Product 1

HCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 16.8%

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-(4-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester (I-26a: 3 g, 13.452 mmol) in POCl3 (30 mL) was reacted with P2O5 (3.793 g, 26.905 mmol). The resulting mixture was stirred at 110° C. for 1 hour to afford the crude product. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 400 mg of the product (16.8% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-7fc2ff6a67d841ffa5fc505764b913f6
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…