Ethyl Acetate → HCID 59536382, compound

HRID 445300Notes

Reaction equation

HRID 445300 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(OCC)(=O)C.[OH-].[K+]>O>[F:1][C:2]1[CH:22]=[C:21]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 7935360HCID 7935360, compound

Product 1

HCID 59536382HCID 59536382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A suspension of N-(4-fluorophenethyl)-4-(trifluoromethyl)benzamide (5.3 g, 17.1 mmol) and phosphoric pentoxide (1.2 g, 8.6 mmol) in polyphosphoric acid (40 g) was heated at 165° C. for 4 h and The reaction was cooled to RT and ice was added followed by ethyl acetate (100 mL), KOH (3N, 25 mL), and water (75 mL). The mixture was stirred for 15 min and the organic layer was separated. The aqueous layer was neutralized with KOH (3N) till pH˜7.0 was achieved and extracted with ethyl acetate (250 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, and concentrated under vacuum to provide 7-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline. MS (ESI pos. ion) m/z: 294 (M+H).

Workup

  1. temperatureThe reaction was cooled to RT
  2. additionice was added
  3. customthe organic layer was separated
  4. extractionextracted with ethyl acetate (250 mL)
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-31755f9611e04a369abe0d3ce63a8ef3
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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