Trifluoroacetic acid → 1,2-Dimethyl-4-(3,4,5-trimethoxyphenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone

HRID 1666315Notes

Reaction equation

HRID 1666315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13](OC(=O)C)[C:14]([N:16]([CH3:27])[CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH3:18])=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>ClCCl>[CH3:18][CH:17]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:14](=[O:15])[N:16]1[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670818362-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-[1-(3-methoxyphenyl)ethyl]acetamide

Product 1

HCID 670818071,2-Dimethyl-4-(3,4,5-trimethoxyphenyl)-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the amide from step 2 above (4.2 g) in dichloromethane (60 ml) and trifluoroacetic acid (20 ml) was refluxed for 4 hours. The reaction mixture was concentrated to dryness and the residue was submitted to chromatography on silica gel using dichloromethane-ethyl acetate (6:4) as eluent. The first fraction was concentrated to dryness and the residue was crystallized from methanol giving diastereomer I, m.p. 135-140° C. The third fraction contained diastereomer II, which was recovered as an amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. concentrationThe first fraction was concentrated to dryness
  3. customthe residue was crystallized from methanol giving diastereomer I, m.p. 135-140° C
  4. customwas recovered as an amorphous solid

Sources & evidence

ORD record
ord-03d6e31726504a90885bfe888c290856
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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