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

HRID 1843822Notes

Reaction equation

HRID 1843822 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[Br: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 15171981Ethyl [2-(4-bromophenyl)ethyl]carbamate

Product 1

HCID 250673307-Bromo-3,4-dihydroisoquinolin-1(2H)-oneYield 12,033.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Using analogous reaction conditions and workup as described in Example 1, step 4, [2-(4-bromo-phenyl)-ethyl]-carbamic acid ethyl ester (I-3c: 5 g, 0.01838 mmol) in POCl3 (20 mL) was reacted with P2O5 (5.2 g, 0.03676 mmol) to afford the crude product. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 500 mg of the product (12% yield).

Workup

  1. customreaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (50% ethylacetate in hexane)

Sources & evidence

ORD record
ord-fe6c5c902ed74a1aa516865fe1825258
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…