Phosphorus oxychloride → 1-(4-Bromo-phenyl)-6-methoxy-3,4-dihydro-isoquinoline

HRID 342213Notes

Reaction equation

HRID 342213 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 110241034-bromo-N-[2-(3-methoxyphenyl)ethyl]benzamide

Product 1

HCID 118232271-(4-Bromo-phenyl)-6-methoxy-3,4-dihydro-isoquinolineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

50 g of 4-bromo-N-[2-(3-methoxy-phenyl)-ethyl]-benzamide are dissolved in 750 ml of acetonitrile and treated under argon with 55 ml of phosphorus oxychloride. After heating to 80° C. the majority of the solvent is removed and the residue is adjusted to pH >12 with concentrated ammonia solution and extracted with ethyl acetate. The organic extracts are washed with saturated sodium chloride solution, dried and concentrated. There are obtained 46.4 g of 1-(4-bromo-phenyl)-6-methoxy-3,4-dihydro-isoquinoline, MS: m/e 314 (M+, 1 Br).

Workup

  1. customis removed
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c096a90b0d2415aa2a62ef2d2d818ef
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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