Sodium Hydroxide → 1-(2-Bromophenyl)-3,4-dihydroisoquinoline

HRID 84129

Reaction equation

HRID 84129 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Br:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Br:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:7][CH2:8][N:9]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 6738402-bromo-N-(2-phenylethyl)benzamide

Product 1

HCID 107795371-(2-Bromophenyl)-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 50.0 g (164 mmol) of N-phenylethyl-2-bromobenzamide and 27.9 g of phosphorus pentoxide in 200 ml of xylene was heated to 100° C. and admixed dropwise with 45.6 g (492 mmol) of phosphorus oxychloride. Subsequently, the reaction mixture was heated under reflux for 2 h. After cooling to 80° C., the reaction mixture was stirred into 4000 g of ice and adjusted to pH=12 with NaOH (solid). The organic phase was removed, the aqueous phase was extracted three times with 300 ml of toluene, and the combined organic phases were washed with 500 ml of water and subsequently dried over magnesium sulfate. After the desiccant had been filtered off and the solvent had been removed, the product was obtained as a yellow oil. The yield at a purity of approx. 99.0% was 46.9 g (164 mmol), 99.9% of theory.

Workup

  1. temperatureSubsequently, the reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling to 80° C.
  4. customThe organic phase was removed
  5. extractionthe aqueous phase was extracted three times with 300 ml of toluene
  6. washthe combined organic phases were washed with 500 ml of water
  7. dry with materialsubsequently dried over magnesium sulfate
  8. filtrationAfter the desiccant had been filtered off
  9. customthe solvent had been removed
  10. customthe product was obtained as a yellow oil
  11. customThe yield at a purity of approx. 99.0%

Sources & evidence

ORD record
ord-29b20c634de1471982541f0e6d40829f
Source dataset
uspto-grants-2014_09
Patent number
US08846920B2

Linked notes

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