Sodium Hydroxide → 4-Methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

HRID 445289

Reaction equation

HRID 445289 reaction equation
[C:1]1([CH:7]([CH3:22])[CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:22][CH:7]1[C:1]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:9][CH2:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 24636638N-(2-phenylpropyl)-4-(trifluoromethyl)benzamide

Product 1

HCID 595364124-Methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 250-mL round-bottomed flask was charged with N-(2-phenylpropyl)-4-(trifluoromethyl)benzamide (5.19 g, 16.9 mmol), phosphorous pentoxide (4.8 g, 33.8 mmol) and toluene (75 mL). The reaction mixture was heated at 110° C. overnight and allowed to cool down to RT. Then it was poured over ice-water and neutralized with NaOH (10%). The organic phase was separated and the aqueous phase was extracted several times with EtOAc. The combined organics were washed with satd. NaHCO3, water, brine and dried over Na2SO4. The solvent was removed under vacuum and the product used without further purification.

Workup

  1. temperatureto cool down to RT
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted several times with EtOAc
  4. washThe combined organics were washed with satd
  5. dry with materialNaHCO3, water, brine and dried over Na2SO4
  6. customThe solvent was removed under vacuum
  7. customthe product used without further purification

Sources & evidence

ORD record
ord-8718eb3ae0a34fa1baec7f00e89daf85
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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