Phosphorus oxide (P4O10) → 5-Chloro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843848Notes

Reaction equation

HRID 1843848 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[Cl:14])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[Cl: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 66807304HCID 66807304, compound

Product 1

HCID 183695065-Chloro-3,4-dihydroisoquinolin-1(2H)-oneYield 9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Using an analogous procedure and workup as described in Example 1, step 4, [2-(2-chloro-phenyl)-ethyl]-carbamic acid ethyl ester (I-12c: 1.4 g, 6.167 mmol) in POCl3 (14 mL) was reacted with P2O5 (1.75 g, 12.334 mmol). The resulting mixture was heated to reflux for 1 hour to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM) afforded 100 mg of the product (9% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (2% methanol in DCM)

Sources & evidence

ORD record
ord-04dfbbbc84dd4f93a46cd4c80881ebc1
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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