Phosphorus oxide (P4O10) → 6-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843867Notes

Reaction equation

HRID 1843867 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[C:4](=[O:3])[NH:5][CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 66804010HCID 66804010, compound

Product 1

HCID 668017026-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-oneYield 15.74%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
105 °C

Procedure

Using the same procedure and workup as described in Example 1, step 4, [2-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester (I-17b: 2.7 g, 10.34 mmol) in POCl3 (15 mL) was reacted with P2O5 (2.9 g, 20.68 mmol). The resulting mixture was stirred at 105° C. for 2 hours to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 350 mg of the product (15.74% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

Sources & evidence

ORD record
ord-baf275b8495649e99c7cc3ef72e90c33
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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