Ethyl Acetate → HCID 59536399, compound

HRID 445292Notes

Reaction equation

HRID 445292 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(OCC)(=O)C.[OH-].[K+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 14797Potassium HydroxideHCID 14812Phosphorus oxide (P4O10)2×HCID 8643478HCID 8643478, compound

Product 1

HCID 59536399HCID 59536399, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A suspension of N-(2-fluorophenethyl)-4-(trifluoromethyl)benzamide (2.0 g, 6.5 mmol) and phosphoric pentoxide (2.7 g, 19.1 mmol) in anhydrous toluene (40 mL) was heated at 125° C. for 4 h. At this stage more phosphoric pentoxide (2.7 g, 19.1 mmol) was added and continued stirring the reaction at 125° C. for additional 16 h. The reaction was cooled to RT, added ethyl acetate (100 mL), and the resulting slurry was slowly poured into ice-water (100 mL). Then more ethyl acetate (75 mL) was added and the resulting suspension was treated with KOH (3.0 N) until pH˜11.0 was achieved. The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, and concentrated under vacuum to provide 5-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline as a yellow oil. MS (ESI pos. ion) m/z: 294 (M+H).

Workup

  1. customthe reaction at 125° C. for additional 16 h
  2. temperatureThe reaction was cooled to RT
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c45019402f0d4c71a4a326bd11f050d4
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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